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Scalable electrochemical reduction of sulfoxides to sulfides
A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.
Kong, Zhenshuo,Pan, Chao,Li, Ming,Wen, Lirong,Guo, Weisi
supporting information
p. 2773 - 2777
(2021/04/21)

Straightforward chemoselective access to unsymmetrical dithioacetals through a thiosulfonate homologation-nucleophilic substitution sequence
A sequential C1-homologation-nucleophilic substitution tactic is presented for the preparation of rare unsymmetrical dithioacetals. The judicious selection of thiosulfonates as convenient sulfur electrophilic sources - upon the homologation event conducted on an intermediate a-halothioether - guarantees the release of the non-reactive sulfonate group, thus enabling the subsequent nucleophilic displacement with an external added thiol [(hetero)- aromatic and/or aliphatic]. Uniform high yields and excellent chemocontrol were deduced during the extensive scope study, thus documenting the versatility of the direct technique for the preparation of these unique and manipulable materials.
Ielo, Laura,Pillari, Veronica,Gajic, Natalie,Holzer, Wolfgang,Pace, Vittorio
p. 12395 - 12398
(2020/10/30)

Consecutive C1-Homologation / Displacement Strategy for Converting Thiosulfonates into O,S-Oxothioacetals
A conceptually intuitive synthesis of oxothioacetals is reported starting from thiosulfonates as electrophilic sulfur donors. The installation of a reactive CH2Cl motif with a homologating carbenoid reagent, followed by the immediate nucleophilic displacement with alcoholic groups [(hetero)-aromatic, aliphatic] offer a convenient access to the title compounds. Genuine chemoselectivity is uniformly observed in the case of multi-functionalized systems. (Figure presented.).
Ielo, Laura,Pillari, Veronica,Miele, Margherita,Holzer, Wolfgang,Pace, Vittorio
p. 5444 - 5449
(2020/10/12)

Sc(OTf)3-Catalyzed Synthesis of Symmetrical Dithioacetals and Bisarylmethanes Using Nitromethane as a Methylene Source
Use of nitromethane as an electrophilic methylene source for the synthesis of symmetrical dithioacetals and bisarylmethanes has been showcased using Sc(OTf)3 as a catalyst. The procedure allows straightforward access to the densely functionalized dithioacetals and bisarylmethanes under mild conditions. Additionally, the method has been applied for the synthesis of antimalarial tetramethyl mellotojaponin C and anticancer dimeric phloroglucinol derivative.
Dethe, Dattatraya H.,Shukla, Manmohan,Dherange, Balu D.
supporting information
p. 5778 - 5782
(2020/07/30)

A thioether compound and its synthetic method and application (by machine translation)
The invention belongs to the technical field of sulfur-containing organic synthesis, discloses a thioether compound and its synthetic method and application. The vinyl ether compound is acetone, b of sulfur compounds, inorganic alkali and 18 - crown ether - 6 mixing, heating and stirring, in the inorganic alkali under the action of the catalyst, the reaction under air atmosphere, and then concentrated, purified made, the vinyl ether compound of molecular formula as formula (1) as shown: Wherein R1 And R2 Selected from hydrogen atom, alkyl, alkoxy, nitro, amino, hydroxy, halogen base, acyl, aryl or a heterocyclic group. The method can avoid the toxicity is relatively large of the methylene chloride and halogenated hydrocarbon such as methylene diiodide. The synthesis step is simple, convenient and easy operation, environment friendly and under a comparatively mild condition, have high conversion, the yield of the product can be as high as 96%. The thioether compound can be applied to the production of organic synthetic intermediates in the field. (by machine translation)
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Paragraph 0036; 0037; 0039; 0041; 0048; 0049

(2018/12/02)

Reduction of CO2 into Methylene Coupled with the Formation of C-S Bonds under NaBH4/I2 System
A selective four-electron reduction of CO2 with thiophenol using NaBH4 as a reductant is described to access dithioacetals. This reaction provides a novel synthetic method for the highly selective conversion of CO2 into methylene, and a new access to molecular structures via formation of C-S bonds using CO2 as the C1 source.
Guo, Zhiqiang,Zhang, Bo,Wei, Xuehong,Xi, Chanjuan
p. 6678 - 6681
(2018/10/24)

Cs2CO3-promoted methylene insertion into disulfide bonds using acetone as a methylene source
An efficient halogen-free Cs2CO3-promoted methylene insertion into disulfide bonds has been achieved using acetone as a methylene source under mild conditions. This method provides a convenient and practical route to dithioacetals in up to 96% yield with good functional group compatibility.
Chen, Qian,Yu, Guodian,Wang, Xiaofeng,Huang, Yulin,Yan, Yan,Huo, Yanping
supporting information
p. 4086 - 4089
(2018/06/12)

Photocatalytic Oxygenation of Sulfide and Alkenes by Trinuclear Ruthenium Clusters
Trinuclear Ru cluster photocatalysts that contain two Ru(II) photosensitizers and a Ru(II) reaction center are prepared, and their activity in the photocatalytic oxygenation of a sufide and alkenes is investigated. Photoirradiation (visible light) and the use of a Co salt ([Co(NH3)5Cl]Cl2, as an electron acceptor) are found to be essential for these catalytic reactions. The O atom of the water solvent (pH 6.8) is transferred to the substrate by a stepwise electron transfer and deprotonation of an aqua ligand at the reaction center. Through these processes, the aqua ligand coordinated at the reaction center is converted to a RuV=O species, which is the active intermediate in the sulfide and alkene oxygenation.
Phungsripheng, Siwas,Kozawa, Kazuyuki,Akita, Munetaka,Inagaki, Akiko
supporting information
p. 3750 - 3758
(2016/05/19)

Regioselective transition metal- and halogen-free direct dithiolation at C(sp3)-H of nitrotoluenes with diaryl disulfides
Here we describe a potassium tert-butoxide-mediated regioselective direct C-S bond formation at the C(sp3)-H position of nitrotoluenes with disulfides in DMSO at room temperature. The developed reaction generated, in good yields, various dithioacetals having OMe, halogen, and NH2 functionalities at various positions of the arene rings of the disulfides. Interestingly, in the absence of nitrotoluene, diaryl disulfides and diselenides underwent one-carbon homologation to form dithioacetals and diselenoacetals. Synthesized dithioacetals were transformed into 4-nitrobenzaldehyde and 7-(bis(phenylthio)methyl)-1H-indole.
Kumar, Shailesh,Kadu, Rahul,Kumar, Sangit
supporting information
p. 9210 - 9214
(2016/10/13)

Bromomethyllithium-mediated chemoselective homologation of disulfides to dithioacetals
An efficient, chemoselective homologation of disulfides and diselenides to the corresponding dithio- and diselenoacetals has been developed via the addition of bromomethyllithium. Chemoselectivity is fully preserved in the presence of concomitant electrophilic sites decorating the substrates. The synthetic potential of selected dithioacetals has been evaluated in Feringa-Fa?anas-Mastral-type Pd-catalyzed coupling with an organolithium and in the unusual 1,4-addition to a Weinreb amide.
Pace, Vittorio,Pelosi, Azzurra,Antermite, Daniele,Rosati, Ornelio,Curini, Massimo,Holzer, Wolfgang
supporting information
p. 2639 - 2642
(2016/02/18)

A highly efficient heterogeneous rhodium(I)-catalyzed C-S coupling reaction of thiols with polychloroalkanes or alkyl halides under mild conditions
Heterogeneous C-S coupling reaction of thiols with polychloroalkanes or alkyl halides was achieved at 30 or 80 °C in the presence of 5 mol% of an MCM-41-immobilized bidentate phosphine rhodium complex (MCM-41-2P-RhCl(PPh3)) and triethylamine, yielding a variety of formaldehyde dithioacetals, ethylenedithioethers and unsymmetric thioethers in good to excellent yields. This heterogeneous rhodium catalyst can be easily recovered and recycled by simple filtration of the reaction solution and used for at least 10 consecutive trials without significant loss of activity.
Xia, Jianhui,Yao, Ruiya,Cai, Mingzhong
p. 221 - 225
(2015/03/30)

Silver-mediated decarboxylative C-S cross-coupling of aliphatic carboxylic acids under mild conditions
A silver-mediated decarboxylative C-S cross-coupling reaction of aliphatic carboxylic acid is described. This reaction occurs smoothly under mild conditions and shows good tolerance of functional groups. It provides an alternative approach for the synthesis of alkyl aryl sulfides.
Wang, Peng-Fei,Wang, Xiao-Qing,Dai, Jian-Jun,Feng, Yi-Si,Xu, Hua-Jian
supporting information
p. 4586 - 4589
(2015/01/08)

A one-pot stereoselective synthesis of electron-deficient 4-substituted (E, E)-1-arylsulfonylbuta-1,3-dienes and their chemoselective [3+2] cycloaddition with azomethine ylides - A simple synthesis of 1,3,4-trisubstituted pyrrolidines and pyrroles
A simple and efficient method for the synthesis of (E,E)-1-(arylsulfonyl) buta-1,3-dienes bearing electron-withdrawing substituents like cyano and ethoxycarbonyl at position 4, involving a one-pot alkylation of bis(phenylsulfonyl)methane with trans-ethyl 4-bromocrotonate/trans-4- bromocrotononitrile, and elimination of arylsulfinic acid, is described. These dienes undergo facile mono [3+2] cycloaddition with azomethine ylides chemoselectivity to furnish functionalized 1,3,4-trisubstituted pyrrolidines. Oxidation of these cycloadduct with MnO2·SiO2 under mild conditions provides 1,3,4-trisubstituted pyrroles. Georg Thieme Verlag Stuttgart. New York.
Sankar, Ulaganathan,Mahalakshmi, Susarla,Balasubramanian, Kalapattukuppuswamy
supporting information
p. 1533 - 1540
(2013/08/23)

Fe-catalyzed allylic C-C-bond activation: Vinylcyclopropanes as versatile a1,a3,d5-synthons in traceless allylic substitutions and [3 + 2]-cycloadditions
The low-valent iron complex Bu4N[Fe(CO)3(NO)] (TBAFe) catalyzes the allylic C-C-bond activation of electron-poor vinyl cyclopropanes to generate synthetically useful a1,a3,d5-synthons which are prone to undergo multiple consecutive reactions. The versatility of this approach is demonstrated by a traceless allylic substitution and a formal [3 + 2] cycloaddition to give either functionalized acyclic products or densely substituted cyclopentanes and pyrrolidines in high yields and regioselectivities.
Dieskau, Andre P.,Holzwarth, Michael S.,Plietker, Bernd
supporting information; scheme or table
p. 5048 - 5051
(2012/05/05)

Sulfenylation of nitroalkanes and hydroxyaryls
The sulfenylation of nitroalkanes and hydroxyaryls in DMSO using aryl disulfides as sulfenylating reagents was studied. The corresponding arylthionitroalkanes and arylthiohydroxyaryls were obtained in moderate to good yields in very mild conditions, thus improving the reported procedures for the synthesis of these compounds.
Blanco, Guillermo A.,Baumgartner, Maria T.
supporting information; experimental part
p. 7061 - 7063
(2012/01/05)

Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging michael acceptors
Chiral amines with a pyrrolidine framework catalyze the enantioselective conjugate addition of a broad range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to >99% ee. This novel process provides synthetically useful chiral γ-gem-sulfonyl or phosphonyl aldehydes which can be widely functionalized with retention of the enantiomeric excess. Mechanistic insights including DFT calculations are explored in detail.
Sulzer-Mosse, Sarah,Alexakis, Alexandre,Mareda, Jiri,Bollot, Guillaume,Bernardinelli, Gerald,Filinchuk, Yaroslav
supporting information; experimental part
p. 3204 - 3220
(2009/12/03)

A highly efficient carbon-sulfur bond formation reaction via microwave-assisted nucleophilic substitution of thiols to polychloroalkanes without a transition-metal catalyst
An efficient carbon-sulfur bond formation reaction has been developed under microwave irradiation. This reaction affords a novel and rapid synthesis of thioacetals and sulfides under mild conditions. This method is particularly noteworthy given its experimental simplicity and high generality, and no transition-metal catalysts were needed under our conditions.
Cao, Yi-Ju,Lai, Yuan-Yuan,Cao, Hong,Xing, Xiao-Ning,Wang, Xiang,Xiao, Wen-Jing
p. 1529 - 1533
(2007/10/03)

Oxalic acid catalyzed reaction between dithioacetals and acetals. A simple and eco-friendly method for a conversion of a dithioacetal to a carbonyl compound
Oxalic acid catalyzes a reaction between dithioacetals and acetals. This reaction is useful in a new and eco-friendly method to convert dithioacetals to carbonyl compounds.
Miyake, Hideyoshi,Nakao, Yuichi,Sasaki, Mitsuru
p. 6247 - 6250
(2007/10/03)

A formal synthesis of (±)-physostigmine via 3,3-rearrangement of a bis-enamine
A new flexible approach to hexahydropyrrolo[2,3-b]indole system via the [3,3]-sigmatropic rearrangement of 1-(2′-methoxycarbonyl-N- methylvinylamino)skatole, culminating in the synthesis of (±)- desoxyeseroline, is described.
Santos, Paulo F.,Srinivasan, Natarajan,Almeida, Paulo S.,Lobo, Ana M.,Prabhakar, Sundaresan
p. 9147 - 9156
(2007/10/03)

Synthesis of dithioacetals and oxathioacetals with chiral auxiliaries
One-pot synthesis of dithioacetals as well as an efficient method for oxathioacetal is reported. Additionally, some chiral auxiliaries were used to synthesize enantiomerically pure dithioacetals and oxathioacetals.
Zaidi, Javid H.,Naeem, Fazal,Khan, Khalid M.,Iqbal, Rasfaid,Zia-Ullah
p. 2641 - 2653
(2007/10/03)

Reactivity of TEMPO anion as a nucleophile and its applications for selective transformations of haloalkanes or acyl halides to aldehydes
Sodium 2,2,6,6-tetramethylpiperidine-N-oxide (TEMPO-Na +), generated by reduction of TEMPO·with sodium naphthalenide in THF, reacted with alkyl halides or acyl halides to produce O-alkylated or acylated TEMPOs, which were in turn oxidized with mCPBA or reduced with DIBAL-H to afford the corresponding aldehydes, thus accomplishing a new protocol for the halides-carbonyls conversion. Graphical Abstract
Inokuchi, Tsutomu,Kawafuchi, Hiroyuki
p. 11969 - 11975
(2007/10/03)

A convenient and general synthesis of alkyl alkylthiomethyl/aryl arylthiomethyl sulfides and chiral sulfoxides by (camphorsulfonyl)oxaziridines
A convenient efficient procedure for the synthesis of thiomethyl sulfides and their reactions with enantiomerically pure (camphorsulfonyl) oxaziridines results in formation of enantioselective monosulfoxides.
Chakraborty,Adhikari,Ray
p. 1132 - 1133
(2007/10/03)

Reactivity of Rieke manganese: Synthesis of pyrrolidine and piperidine derivatives
Low-valent manganese generated by the reduction of manganese(II) chloride using lithium naphthalenide (Rieke manganese) promotes reactions of alkyl halides with electrophiles such as acyl chloride, aldehyde, and ketone to afford alkylation products. N-Haloalkyl-N-allyltosylamides are converted to pyrrolidine and piperidine derivatives in high yields. In the reactions of aromatic aldehyde and ketone, pinacol-type coupling products are produced.
Hojo, Makoto,Yoshizawa, Junji,Funahashi, Yoshihiro,Okada, Ryo,Nakamura, Shin-Ya,Tateiwa, Jun-Ichi,Hosomi, Akira
p. 85 - 88
(2007/10/03)

New Synthetic Routes to Unsymmetrical Diorganyl Sulfides
A number of new methods for preparing unsymmetrical diorganyl sulfides was proposed. The methods rely on generation of thiolate anions from thiols, isothiuronium salts, and disulfides in the system hydrazine hydrate-KOH, followed by alkylation of the anions with alkyl halides. The hydrazine hydrate plays the role of medium and reducing agent, which prevents side thiol oxidation. The yield of sulfides reaches 98%. The reaction products are readily separated from the aqueous-hydrazine layer and purified by distillation. The yield of sulfides is reduced by a deficit of alkali and by increasing chain length and functionalization of alkyl groups in the alkyl halide. The reactivity of alkyl halides is independent of the nature of the halogen. From isothiuronium salts, 2-pyridyl sulfides were obtained in the highest yields.
Deryagina,Korchevin,Papernaya
p. 812 - 815
(2007/10/03)

Generation and intramolecular cyclization of α-phenylsulfonyl and α-alkylsulfonyl radicals
α-Phenylsulfonyl radicals are generated by the reaction of diphenyl dithioacetals or phenyl α-chlorosulfides with tributyltin hydride. Alkyl phenyl dithioacetals react selectively with tributyltin hydride to give α-alkylsulfonyl radicals. 5-Exo-type of intramolecular cyclizations of these radicals are studied. The cyclization is most successful when the olefin is terminally substituted with an ester group. The cis/trans ratio of the cyclized product varies according to the reaction rates. With a faster cyclization, cis-isomer is the major product. A slower cyclization gives more trans-product.
Tsai, Yeun-Min,Chang, Fu-Chang,Huang, Jimin,Shiu, Chi-Lung,Kao, Chai-Lin,Liu, Jyh-Shiunn
p. 4291 - 4308
(2007/10/03)

Tin-Pummerer rearrangement in the synthesis of O,S-acetal derivatives
α-Thioalkyl esters and carbonates have been prepared by a tin-Pummerer rearrangement in reactions of α-stannylated sulfoxides with acid chlorides or chloroformates, respectively. Acid chlorides have a higher reactivity than chloroformates in this reaction. Acta Chemica Scandinavica 1997.
Hatlelid, Jostein,Benneche, Tore,Undheim, Kjell
p. 1092 - 1095
(2007/10/03)

Unexpected alkylation reaction of amines, acids and phenols by alkyl (triphenylphosphoranylidene)acetates
Reaction of methyl (triphenylphosphoranylidene)acetate in methanol with primary and secondary amines led to N-methylated derivatives. Similarly this mixture reacted with acids, phenol and phthalimide to afford methyl esters, anisole and N-methylphthalimide respectively. Treatment of ketolactam 2 by this mixture under high pressure activation gave the rearranged quinolinone 5.
Desmaele, Didier
p. 1233 - 1236
(2007/10/03)

Reductive α-substitution of sulfoxides with grignard reagents promoted by a magnesium amide
The reactions of sulfoxides bearing α-hydrogen(s) (RSOCHR1R2: R-alkyl or aryl; R1, R2 = H, alkyl, or aryl) with Grignard reagents (R3MgBr: R3 = Et, Ph, or vinyl) in the presence of the diisopropylaminomagnesium reagent, generated in situ by the treatment of diisopropylamine with the appropriate Grignard reagents in diethyl ether, have resulted in the formation of the corresponding sulfides (RSCR1R2R3) in moderate to good isolated yields.
Kobayashi, Kazuhiro,Yokota, Kouichi,Akamatsu, Hideki,Morikawa, Osamu,Konishi, Hisatoshi
p. 441 - 443
(2007/10/03)

Reactions of Sulfoxides with Magnesium Amides. Transformations of Sulfoxides into Sulfides, Dithioacetals and Vinyl Sulfides
The reactions of sulfoxides with magnesium amides generated in situ from the reaction of ethylmagnesium bromide and seconday amines, such as diisopropylamine (DIPA) or 2,2,6,6-tetramethylpiperidine (TMP) in diethyl ether, were examined.Diaryl sulfoxides were heated with the diisopropylaminomagnesium reagent in diethyl ether to give the corresponding diaryl sulfides in 42-52percent yields.Sulfoxides bearing hydrogens at the α-position only(RSOCH2R1) reacted with the tetramethylpiperidinomagnesium reagent at room temperature to produce the corresponding dithioacetals (RSCHR1SR) in 47-86percent yields.The treatment of sulfoxides bearing hydrogens both at the α-and β-positions (RSOCHR1CHR2R3) with the magnesium amides at room temperature afforded the corresponding vinyl sulfides (RSCR1=CR2R3) in 52-72percent yields accompanying 2.3-27percent yields of the corresponding dithioacetals.The pathways leading to the products involving the formation of the sulfur-stabilized carbonium ion intermediates are discussed.
Kobayashi, Kazuhiro,Kawakita, Masataka,Yokota, Kouichi,Mannami, Tohru,Yamamoto, Koji,et al.
p. 1401 - 1408
(2007/10/02)

Neighbouring Group Effects in a Pummerer-Type Rearrangement: A Facile Entry into 3,1-Benzoxathiins
Arylmethyl sulphoxides treated with trialkylsilyl halide and base undergo a Pummerer-type rearrangement to give α-siloxy and α-chlorosulphides.However, the presence of an ortho hydroxymethyl group results in the exclusive and efficient formation of the α-chlorosulphides, presumably mediated via an intramolecular attack to yield an alkoxysulphonium salt.These 2-(hydroxymethyl)aryl chloromethylsulphides can then be converted into the corresponding 3,1-benzoxathiins via an intramolecular cyclisation.Preliminary investigation of the chemistry of these 3,1-benzoxathiins, reveals that in one case, a novel base induced ring contraction occurs to yield a benzothiophene.
Kersey, Ian D.,Fishwick, Colin W. G.,Findlay, John B. C.,Ward, Peter
p. 6819 - 6834
(2007/10/02)

IMPROVED SYNTHESIS OF FLUOROMETHYL PHENYL SULFONE
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Matthews, Donald P.,Persichetti, Rose A.,McCarthy, James R.
p. 605 - 608
(2007/10/02)

Formation of Dithioacetals by Treatment of Sulfoxides Carrying α-Hydrogens with Magnesium Amides
Sulfoxides carrying α-hydrogens were allowed to react with magnesium amides generated in situ by the treatment of ethylmagnesium bromide with secondary amines such as 2,2,6,6-tetramethylpiperidine or diisopropylamine in diethyl ether to give the corresponding dithioacetals in moderate to good yields.
Kobayashi, Kazuhiro,Kawakita, Masataka,Mannami, Tohru,Morikawa, Osamu,Konishi, Hisatoshi
p. 1551 - 1554
(2007/10/02)

Convenient Synthesis of Phenyl Sulfides by a Borohydride Exchange Resin-Phenyl Disulfide System in Methanol
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Yoon, Nung Min,Choi, Jaesung,Ahn, Jin Hee
p. 3490 - 3493
(2007/10/02)

REACTIONS OF ARENETHIOLS AND 2-THIOPHENETHIOL WITH THE PARAFORM-CHLOROTRIMETHYLSILANE SYSTEM
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Turchaninova, L. P.,Vvedenskii, V. Yu.,Shipov, A. G.,Deryagina, E. N.,Baukov, Yu. I.,Voronkov, M. G.
p. 1722 - 1723
(2007/10/02)

CLAY CATALYSIS: SYNTHESIS OF ORGANOSULPHUR SYNTHONS
The Montmorillonite KSF catalyses the synthesis of a large variety of organic sulphur compounds from carbonyl compounds: dithianes, thioacetals, thioketals,thiochromanes.
Labiad, B.,Villemin, D.
p. 31 - 38
(2007/10/02)

ELECTROCHEMICAL ALKYLATION USING METHYLENE CHLORIDE
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Petrosyan, V. A.,Niyazymbetov, M. E.,Baryshnikova, T. K.,Dorokhov, V. A.
p. 283 - 285
(2007/10/02)

Synthese de lactones a cycle moyen: Application a la synthese du pentadecanolide-15 et du phoracantholide I
Medium ring size lactones can be prepared from bifunctional commercial starting compounds in high yields, using a few step sequence.Lactonisation is obtained by cyclization of the free ω-hydroxyacids or by the cyclization of ω-hydroxyacids having the hydroxy and carboxy group protected.
Cossy, Janine,Pete, Jean-Pierre
p. 989 - 994
(2007/10/02)

Extremely Reactive C=C Double Bonds, VI. - Tris(methylphenylamino)methane - The Chemistry of Orthoamides
Reactions of the title compound 2 with sulfur, selenium, thiophenol, malononitrile, 1,3-indanedione, fluorenone hydrazone, phenylmagnesium bromide, bromine, thioacetic acid, N,N'-diphenylurea, oxalyl chloride, 9,9-dichloroxanthene, phenyl isocyanate, and stilbene dibromide are described and the mechanisms are discussed.The catalytic influence of 2 on the decomposition of 9-diazofluorene in xylene and mesitylene is discussed.
Schoenberg, Alexander,Singer, Erich,Stephan, Werner
p. 1581 - 1588
(2007/10/02)

Studies on the Reactivity of Carbon Monosulfide toward Amines and Thiols
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Moltzen, Ejner K.,Kramer, Michael P.,Senning, Alexander,Klabunde, Kenneth J.
p. 1156 - 1161
(2007/10/02)

Monomethylation of Aromatic Rings by Friedel-Crafts Reaction with Chloromethyl Sulfide
A novel method for the introduction of a methyl group into aromatic rings is described.Friedel-Crafts reactions of ethyl α-(chloromethylthio)acetate (3k) and α-chloromethylthio-γ-butyrolactone (3m) with an arene in the presence of stannic chloride gave ethyl α-(arylmethylthio)acetate (6) and α-arylmethylthio-γ-butyrolactone (7), respectively, which were easily converted to the corresponding methylated arene (8) by reductive desulfurization with Raney nickel or zinc dust-acetic acid.Keywords - monomethylation; ethyl α-(chloromethylthio)acetate Friedel-Crafts reaction; α-chloromethylthio-γ-butyrolactone Friedel-Crafts reaction; ethyl α-(arylmethylthio)acetate; α-arylmethylthio-γ-butyrolactone; methylated arene; reductive desulfurization; Raney nickel; zinc dust-acetic acid
Tamura, Yasumitsu,Annoura, Hirokazu,Fuji, Masahiro,Okura, Masami,Ishibashi, Hiroyuki
p. 540 - 549
(2007/10/02)

Relative Reactivities of Various Sulfides, Selenides and Halides Towards SH2 Attack by Tributyltin Radicals
The order of reactivity towards SH2 attack by tributyltin radicals on various groups X in four different molecular environments (RCO2CH2X, RCH2OCH2X, XCH2CO2Et and RCH2X) has been found by competition experiments to be Br > PhSe > Cl > p-CNC6H4S > PhS > p-MeC6H4S > MeS.The mechanism of the reaction of chloromethyl phenyl sulfide with alkoxides is discussed.
Beckwith, Athelstan L. J.,Pigou, Paul E.
p. 77 - 87
(2007/10/02)

Zur Koordination Mehrfunktioneller Thioether in Cyclopentadienyleisen-Komplexen
+ reacts with the ligands L-L and L-L-L to give the cations + (L-L= RS(CH2)nSR, 1,4-dithiane) and + (L-L-L= 1,3,5-trithiane, tris(methylmercapto)methane) containing monodentate coordinated sulfur ligands.In a similar way, sulfur ligand bridged dinuclear dications 2+ and 2+ and trinuclear trications 3+ are formed.Irradiation of the mononuclear cations gives the chelate complexes 2-L-L)>+.
Kuhn, Norbert,Schumann, Hans
p. 93 - 104
(2007/10/02)

REACTION OF SULFOXIDES WITH NITRILES IN PRESENCE OF TRIFLUOROACETIC ANHYDRIDE AND TRIFLUOROACETIC ACID: A CASE OF RITTER REACTION OF PUMMERER INTERMEDIATE
Reaction of various sulfoxides 9, with nitriles 10 in presence of trifluoroacetic anhydride and trifluoroacetic acid gave the corresponding amides 11 via a Ritter reaction on Pummerer intermediate derived from the sulfoxides.
Vankar, Yashwant D.,Rao, C. Trinadha
p. 3405 - 3410
(2007/10/02)

Preparation of thioethers
A novel process for the preparation of thioethers comprising reacting a silylated thiol of the formula wherein R is an organic group and R1, R2 and R3 are individually selected from the group consisting of alkyl of 1 to 4 carbon atoms with an organic halide, sulfate or sulfonate in the presence of hexamethylphosphoric triamide as a solvent or co-solvent preferably under neutral conditions in aprotic solvents at a temperature between 0° and 150° C.
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(2008/06/13)

Novel Alumina-catalysed Reactions of Arylthioalkyl Halides and Related Compounds
Arylthioalkyl halides of the type ArS(CH2)nCl (Ar = phenyl or substituted phenyl, n = 1-4) undergo rearrangement on heating with neutral alumina to 1,n-bis(arylthio)alkanes of type ArS(CH2)nSAr in high yield.Similar rearrangements occur with some closely related structural types.The bis(arylthio)alkanes undergo further reaction with alumina at higher temperatures in air giving diaryl disulphides.Bis(o-iodophenylthio)methane eliminates iodine on heating with alumina, producing dibenzodithiepin.Some observations concerning the mechanism are presented.
Jigajinni, Veerappa B.,Wightman, Richard H.
p. 1801 - 1812
(2007/10/02)

THIOALKYLATION. VII. CONDENSATION OF 1,3-DISULFONES WITH FORMALDEHYDE AND POTASSIUM HYDROSULFIDE
1,1,5,5-Tetrakis(butylsulfonyl)-, 1,1,5,5,-tetrakis(cyclohexylsulfonyl)-, and 1,1,5,5-tetrakis(phenylsulfonyl)-3-thiapentanes were obtained by the reaction of bis(butylsulfonyl)-, bis(cyclohexylsulfonyl)-, and bis(phenylsulfonyl)methanes respectively with formaldehyde and potassium hydrosulfide in molar ratios of 2:2:1.
Dronov, V. I.,Nigmatullina, R. F.,Makhmutova, I. Kh.,Nikitin, Yu. E.
p. 468 - 470
(2007/10/02)

REACTIONS OF SULFINYL CARBANIONS WITH ORGANOMETALLIC COMPOUNDS: PREPARATION OF
Sulfinyl carbanions, -Li+ (R = Ph, Me; R' = H, Ph) have been observed to have often low reactivity towards neutral transition metal organometallic systems.When reactions do occur they usually involve salt eliminations and
Lucas, C.R.
p. 281 - 292
(2007/10/02)

Complete Regio- and Stereospecificity in the Lewis Acid Catalyzed Diels-Alder Reactions of (Z)-2-Methoxy-1-(phenylthio)-1,3-butadienes. Conversion of the CS Configuration of an Adduct to the CC Configuration at the Allylic Position by a Sigmatropic Rearrangement
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Cohen, Theodore,Kosarych, Zenyk
p. 4005 - 4008
(2007/10/02)

Preparation and Reactions of Some Reagents for Umpolung under Phase-transfer Catalysis
Thioacetals 4a-h are used as reagents for umpolung.They can be prepared in high yields from inexpensive starting materials under phase-transfer catalysis (PTC).H/D-exchange reactions of thioacetals under PTC-conditions are described.Ethyl 1,3-dithiane-2-carboxylate (4a) served as a model compound in order to demonstrate possibilities and limitations of PTC-deprotonation and subsequent reaction with electrophiles compared with other procedures.
Lissel, Manfred
p. 1589 - 1601
(2007/10/02)

Reaction of Pummerer Rearrangement Intermediates with Sulfides and Thiols. Synthesis of Sulfonium Salts and Dithioacetals
Sulfides (5) and thiols (6) react instantly with the Pummerer rearrangement intermediates (3) at 0 deg C to give sulfonium salts (7) and dithioacetals (8), respectively.
Tanikaga, Rikuhei,Hiraki, Yuji,Ono, Noboru,Kaji, Aritsune
p. 41 - 42
(2007/10/02)