- Direct Arylation of Distal and Proximal C(sp3)-H Bonds of t-Amines with Aryl Diazonium Tetrafluoroborates via Photoredox Catalysis
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A visible light-mediated arylation protocol for t-amines has been reported through the coupling of γ- and α-amino alkyl radicals with different aryl diazonium salts using Ru(bpy)3Cl2·6H2O as a photocatalyst. Structurally different 9-aryl-9,10-dihydroacridine, 1-aryl tetrahydroisoquinoline, hexahydropyrrolo[2,1-a]isoquinoline, and hexahydro-2H-pyrido[2,1-a]isoquinoline frameworks with different substitution patterns have been synthesized in good yield using this methodology.
- Mondal, Pradip Kumar,Tiwari, Sandip Kumar,Singh, Pushpendra,Pandey, Ganesh
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p. 17184 - 17196
(2021/12/02)
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- Exploring the Potential of 2-(2-Nitrophenyl)ethyl-Caged N-Hydroxysulfonamides for the Photoactivated Release of Nitroxyl (HNO)
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The emergence of nitroxyl (HNO) as a biological signaling molecule is attracting increasing attention. HNO-based prodrugs show considerable potential in treating congestive heart failure, with HNO reacting rapidly with metal centers and protein-bound and free thiols. A new class of 2-(2-nitrophenyl)ethyl (2-NPE)-photocaged N-hydroxysulfonamides has been developed, and the mechanisms of photodecomposition have been investigated. Three photodecomposition pathways are observed: The desired concomitant C-O/N-S bond cleavage to generate HNO, sulfinate, and 2-nitrostyrene, C-O bond cleavage to give the parent sulfohydroxamic acid and 2-nitrostyrene, and O-N bond cleavage to release a sulfonamide and 2-nitrophenylacetaldehyde. Laser flash photolysis experiments provide support for a Norrish type II mechanism involving 1,5-hydrogen atom abstraction to generate an aci-nitro species. A mechanism is proposed in which the (Z)-aci-nitro intermediate undergoes either C-O bond cleavage to release RSO2NHO(H), concerted C-O/N-S bond cleavage to generate sulfinate and HNO, or isomerization to the (E)-isomer prior to O-N bond cleavage. The pKa of the N(H) of the N-hydroxysulfonamide plays a key role in determining whether C-O or concerted C-O/N-S bond cleavage occurs. Deprotonating this site favors the desired C-O/N-S bond cleavage at the expense of an increased level of undesired O-N bond cleavage. Triplet state quenchers have no effect on the observed photoproducts.
- Bharadwaj, Vinay,Brasch, Nicola E.,Rahman, Mohammad S.,Sampson, Paul,Seed, Alexander J.
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p. 16448 - 16463
(2021/12/06)
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- Synthesis of thioethers, arenes and arylated benzoxazoles by transformation of the C(aryl)-C bond of aryl alcohols
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Transformation of aryl alcohols into high-value functionalized aromatic compounds by selective cleavage and functionalization of the C(aryl)-C(OH) bond is of crucial importance, but very challenging by far. Herein, for the first time, we report a novel and versatile strategy for activation and functionalization of C(aryl)-C(OH) bonds by the cooperation of oxygenation and decarboxylative functionalization. A diverse range of aryl alcohol substrates were employed as arylation reagents via the cleavage of C(aryl)-C(OH) bonds and effectively converted into corresponding thioether, arene, and arylated benzoxazole products in excellent yields, in a Cu based catalytic system using O2 as the oxidant. This study offers a new way for aryl alcohol conversion and potentially offers a new opportunity to produce high-value functionalized aromatics from renewable feedstocks such as lignin which features abundant C(aryl)-C(OH) bonds in its linkages.
- Chen, Bingfeng,Han, Buxing,Liu, Mingyang,Meng, Qinglei,Song, Jinliang,Zhang, Pei,Zhang, Zhanrong
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p. 7634 - 7640
(2020/08/14)
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- Antiproliferative activity and SARs of caffeic acid esters with mono-substituted phenylethanols moiety
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A series of CAPE derivatives with mono-substituted phenylethanols moiety were synthesized and evaluated by MTT assay on growth of 4 human cancer cell lines (Hela, DU-145, MCF-7 and ECA-109). The substituent effects on the antiproliferative activity were systematically investigated for the first time. It was found that electron-donating and hydrophobic substituents at 2′-position of phenylethanol moiety could significantly enhance CAPE's antiproliferative activity. 2′-Propoxyl derivative, as a novel caffeic acid ester, exhibited exquisite potency (IC50?=?0.4?±?0.02 & 0.6?±?0.03?μM against Hela and DU-145 respectively).
- Xie, Jin,Yang, Fengzhi,Zhang, Man,Lam, Celine,Qiao, Yixue,Xiao, Jia,Zhang, Dongdong,Ge, Yuxuan,Fu, Lei,Xie, Dongsheng
-
supporting information
p. 131 - 134
(2016/12/27)
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- Pd-Catalyzed Selective Synthesis of Cyclic Sulfonamides and Sulfinamides Using K2S2O5 as a Sulfur Dioxide Surrogate
-
A variety of cyclic sulfonamides and sulfinamides could be selectively synthesized under Pd catalysis using haloarenes bearing amino groups and a sulfur dioxide (SO2) surrogate. The amount of base was key in determining the selectivity. Mechanistic studies revealed that sulfinamides were initially formed via an unprecedented formal insertion of sulfur monoxide and were oxidized to sulfonamides in the presence of an iodide ion and DMSO.
- Konishi, Hideyuki,Tanaka, Hiromichi,Manabe, Kei
-
supporting information
p. 1578 - 1581
(2017/04/13)
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- Process for Synthesis of Chiral 3-Substituted Tetrahydroquinoline Derivatives
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The present invention relates to novel and concise process for the construction of chiral 3-substituted tetrahyroquinoline derivatives based on proline catalyzed asymmetric α-functionalization of aldehyde, followed by in situ reductive cyclization of nitro group under catalytic hydrogenation condition with high optical purities. Further the invention relates to conversion of derived chiral 3-substituted tetrahydroquinoline derivatives into therapeutic agents namely (?)-sumanirole (96% ee) and 1-[(S)-3-(di-methylamino)-3,4-dihydro-6,7-dimethoxy-quinolin-1(2H)-yl]propanone[(S)-903] (92% ee).
- -
-
Paragraph 0047; 0082; 0083
(2015/02/19)
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- Asymmetric Intramolecular Conjugate Addition Nitro-Mannich Route to cis-2-Aryl-3-nitrotetrahydroquinolines
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Reductive cyclization of 2-iminonitrostyrenes (from the condensation of 2-aminostyrenes with an aldehyde and subsequent nitration of the alkene) using a bifunctional thiourea catalyst and tert-butyl-Hantzsch ester leads to an intramolecular conjugate hydride addition nitro-Mannich reaction to give the corresponding cis-2-aryl-3-nitrotetrahydroquinolines as single diastereoisomers in high yields and enantioselectivities.
- Anderson, James C.,Barham, Joshua P.,Rundell, Christopher D.
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p. 4090 - 4093
(2015/09/01)
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- Palladium-catalyzed direct coupling of 2-vinylanilines and isocyanides: An efficient synthesis of 2-aminoquinolines
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Palladium-catalyzed oxidative coupling of 2-vinylanilines and isocyanides constitutes a direct, facile, and efficient approach to 2-aminoquinolines. The procedure, employing palladium acetate and silver carbonate, is attractive in terms of assembly efficiency, functional group tolerance, and operational simplicity. A variety of 2-aminoquinolines were prepared in good to excellent yields.
- Wang, Lijie,Ferguson, Jamie,Zeng, Fanlong
-
supporting information
p. 11486 - 11491
(2015/12/04)
-
- CERTAIN PROTEIN KINASE INHIBITORS
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Provided are certain EGFR mutant selective inhibitors, pharmaceutical compositions thereof, and methods of use therefor.
- -
-
Paragraph 00401-00403
(2016/01/01)
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- Synthesis of indolines via a SmI2 promoted domino nitro reduction-intramolecular aza-Michael reaction
-
A simple and straightforward synthesis of substituted indolines based on a domino nitro reduction intramolecular aza-Michael reaction is described. The reaction employs Samarium diiodide under mild conditions for the addition of dibromoacetic acid to substituted 2-(2-nitrophenyl) acetaldehyde derivatives and their subsequent cyclization upon nitro group reduction to provide corresponding indoline heterocycles in good yields. This "one pot" strategy also permitted the expeditious synthesis of a 1,2,3,4-tetrahydroquinoline, whereas the seven-membered 2,3,4,5-tetrahydrobenzoazepines compounds were not formed under these reaction conditions.
- Ramos, Josierika A. Ferreira,Araújo, Carolina S.,Nagem, Tanus J.,Taylor, Jason G.
-
-
- A PROCESS FOR SYNTHESIS OF CHIRAL 3-SUBSTITUTED TETRAHYDROQUINOLINE DERIVATIVES
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The present invention relates to novel and concise process for the construction of chiral 3-substituted tetrahydroquinoline derivatives based on proline catalyzed asymmetric α-functionalization of aldehyde, followed by in situ reductive cyclization of nitro group under catalytic hydrogenation condition with high optical purities. Further the invention relates to conversion of derived chiral 3-substituted tetrahydroquinoline derivatives into therapeutic agents namely (-)-sumanirole (96% ee) and 1-[(S)-3-(dimethylamino)-3,4-dihydro-6,7-dimethoxy-quinolin-1(2H)-yl]propanone[(S)-903] (92% ee).
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-
Page/Page column 32-33
(2013/10/08)
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- Pyrrolidinyl phenylurea derivatives as novel CCR3 antagonists
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Optimization starting with our lead compound 1 (IC50 = 4.9 nM) led to the identification of pyrrolidinyl phenylurea derivatives. Further modification toward improvement of the bioavailability provided (R)-1-(1-((6-fluoronaphthalen-2-yl)methyl)pyrrolidin-3-yl)-3-(2-(2- hydroxyethoxy)phenyl)urea 32 (IC50 = 1.7 nM), a potent and orally active CCR3 antagonist.
- Nitta, Aiko,Iura, Yosuke,Inoue, Hideki,Imaoka, Takayuki,Takahashi, Toshiya,Sato, Ippei,Morihira, Koichiro,Kubota, Hirokazu,Morokata, Tatsuaki,Takeuchi, Makoto,Ohta, Mitsuaki,Tsukamoto, Shin-Ichi
-
p. 6876 - 6881,6
(2020/09/02)
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- Convenient and scalable process for the preparation of indole via raney nickel-catalyzed hydrogenation and ring closure
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An efficient and practical method for the synthesis of indole as a key starting material for many useful chemicals is described. Using 2-nitrotoluene as starting material, hydroxymethylation with formaldehyde under alkaline conditions gave 2-(2-nitrophenyl) ethanol on a large scale. Raney Ni catalyst was used for both reduction of the nitro group as well as for the indole formation. The overall yield was 78% from 2-nitrotoluene. Copyright
- Guo, Xianghai,Peng, Zhiliang,Jiang, Shende,Shen, Jiaxiang
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scheme or table
p. 2044 - 2052
(2011/08/03)
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- An unusual route to a quinoline 1-oxide via intramolecular addition of an enolate to an aromatic nitro group
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A mixture of ethyl 4-(2-nitrophenyl)butenoates undergoes an unusual intramolecular cyclisation in the presence of a catalytic amount of potassium tert-butoxide. 2011 · Copyright by Walter de Gruyter.
- Moreira, Nayara Da Rocha F.,De Oliveira, Tania T.,Nagem, Tanus J.,Taylor, Jason G.
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scheme or table
p. 203 - 205
(2012/03/12)
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- Chromo-fluorogenic detection of nerve-agent mimics using triggered cyclization reactions in push-pull dyes
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A family of azo and stilbene derivatives (1-9) are synthesized, and their chromo-fluorogenic behavior in the presence of nerve-agent simulants, diethylchlorophosphate (DCP), diisopropylfluorophosphate (DFP), and diethylcyanophosphate (DCNP) in acetonitrile and mixed solution of water/acetonitrile (3:1 v/v) buffered at pH 5.6 with MES, is investigated. The prepared compounds contain 2-(2-N,N-dimethylaminophenyl) ethanol or 2-[(2-N,N-dimethylamino)phenoxy]ethanol reactive groups, which are part of the conjugated π-system of the dyes and are able to give acylation reactions with phosphonate substrates followed by a rapid intramolecular N-alkylation. The nerve-agent mimic-triggered cyclization reaction transforms a dimethylamino group into a quaternary ammonium, inducing a change of the electronic properties of the delocalized systems that results in a hypsochromic shift of the absorption band of the dyes. Similar reactivity studies are also carried out with other "non-toxic" organophosphorus compounds, but no changes in the UV/Vis spectra were observed. The emission behaviour of the reagents in acetonitrile and water-acetonitrile 3:1 v/v mixtures is also studied in the presence of nerve-agent simulants and other organophosphorous derivatives. The reactivity between 1-9 and DCP, DCNP, or DFP in buffered water-acetonitrile 3:1 v/v solutions under pseudo first-order kinetic conditions, using an excess of the corresponding simulant, are studied in order to determine the rate constants (k) and the half-life times (t1/2=ln2/k) for the reaction. The detection limits in water/acetonitrile 3:1 v/v are also determined for 1-9 and DCP, DCNP, and DFP. Finally, the chromogenic detection of nerve agent simulants both in solution and in gas phase are tested using silica gel containing adsorbed compounds 1, 2, 3, 4, or 5 with fine results.
- Costero, Ana M.,Parra, Margarita,Gil, Salvador,Gotor, Raffll,Mancini, Pedro M. E.,Martinez-Macez, Ramon,Sancenon, Felix,Royo, Santiago
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experimental part
p. 1573 - 1585
(2011/08/05)
-
- Chromogenic detection of nerve agent mimics
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A new chromogenic protocol for the selective detection of nerve agent mimics is reported. The Royal Society of Chemistry.
- Costero, Ana M.,Gil, Salvador,Parra, Margarita,Mancini, Pedro M. E.,Martinez-Manez, Ramon,Sancenon, Felix,Royo, Santiago
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experimental part
p. 6002 - 6004
(2009/05/06)
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- 5′-(2-Nitrophenylalkanoyl)-2′-deoxy-5-fluorouridines as potential prodrugs of FUDR for reductive activation
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Four 5′-(2-nitrophenylalkanoyl)-2′-deoxy-5-fluorouridines (1a-d) were designed and synthesized as potential prodrugs of FUDR for reductive activation. Two methyl groups were introduced α to the ester carbonyl to increase both the rate of cyclization activation and the stability of the conjugates towards serum esterases. Chemical reduction of the nitro group into an amino leads to cyclization and release of the active FUDR. Kinetic analysis of the cyclization activation process indicates that the two methyl groups α to the ester carbonyl restrict the rotational freedom of ground state molecule and promote the cyclization reaction. However, the two methyl groups also were found to render the conjugates as poor substrates of E. coli B nitroreductase. Conjugate 1c, without the two methyl groups, was reduced by E. coli B nitroreductase (t1/2=8 h) to give two products, a N-hydroxyl lactam and the drug FUDR, suggesting that the enzymatic reduction and subsequent cyclization activation proceeded through the hydroxylamine intermediate. These results indicate that cyclization activation will occur once the nitro group is reduced either to an amino or to a hydroxylamino group. The fact that the amino intermediates cyclized easily to release the incorporated drug FUDR suggests the feasibility of using peptide-linked acyl 2-aminophenylalkanoic acid esters as potential prodrugs for proteolytic activation.
- Liu, Bin,Hu, Longqin
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p. 3889 - 3899
(2007/10/03)
-
- Radical ring closures of 4-isocyanato carbon-centered radicals
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The 2-(2-isocyanatophenyl)ethyl radical was generated from the corresponding bromide with tributyltin and tris(trimethylsilyl)silyl radicals and shown to ring close in the 6-endo-mode to afford 3,4-dihydro-1H-quinolin-2-one as the major product. Cyclization in the 5-exo-mode to produce 2,3-dihydroindole-1-carbaldehyde, after hydrogen abstraction, was a minor reaction. Rate constants for the two processes were estimated and compared with reaction enthalpies computed by the DFT method.
- Minin, Patricia L.,Walton, John C.
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p. 2960 - 2963
(2007/10/03)
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- Intramolecular 1,3-dipolar cycloaddition strategy for enantioselective synthesis of FR-900482 analogues
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(Equation presented) Enantioselective synthesis of FR-900482 analogues is described. The key reaction of the synthesis is intramolecular 1,3-dipolar cycloaddition of a highly functionalized nitrile oxide with complete stereo-and regioselectivities to construct the eight-membered benzazocine ring.
- Kambe, Mika,Arai, Eri,Suzuki, Masashi,Tokuyama, Hidetoshi,Fukuyama, Tohru
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p. 2575 - 2578
(2007/10/03)
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- Nucleoside derivatives with photolabile protective groups
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The invention relates to nucleoside derivatives having photolabile protective groups of the general formula (I) STR1 in which R1 =H, NO2, CN, OCH3, halogen or alkyl or alkoxyalkyl having 1 to 4 C atoms R2 =H, OCH3 R3 =H, F, Cl, Br, NO2 R4 =H, halogen, OCH3, or an alkyl radical having 1 to 4 C atoms R5 =H or a usual functional group for preparing oligonucleotides R6 =H, OH, halogen or XR8, where X=O or S and R8 represents a protective group usual in nucleotide chemistry, B=adenine, cytosine, guanine, thymine, uracil, 2,6-diaminopurin-9-yl, hypoxanthin-9-yl, 5-methylcytosin-1-yl, 5-amino-4-imidazolcarboxamid-1-yl, or 5-amino-4-imidazolcarboxamid-3-yl, where in the case of B=adenine, cytosine or guanine, the primary amino function optionally exhibits a permanent protective group. These derivatives may be used for the light-controlled synthesis of oligonucleotides on a DNA chip.
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- New photolabile protecting groups in nucleoside and nucleotide chemistry - Synthesis, cleavage mechanisms and applications
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New photolabile protecting groups have been found in the 2-(2- nitrophenyl)ethoxycarbonyl and the 2-(2-nitrophenyl)ethylsulfonyl group, respectively. The influence of substituents at the phenyl ring as well as the side-chain has been investigated regarding the photolysis rates on irradiation at 365 mn. β-Branching in the side-chain leads to highly increased rates of photodeprotection. A new type of photocleavage mechanism consisting of a photoinduced β-elimination process is proposed.
- Giegrich,Eisele-Buehler,Hermann,Kvasyuk,Charubala,Pfleiderer
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p. 1987 - 1996
(2007/10/03)
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- Synthesis of terphenylboronic acid derivatives and recognition of anomers of 2-deoxyribofuranoside
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A terphenylboronic acid 1 and its silylated derivative 2 are prepared from (2-nitrophenyl)acetic acid for the purpose of controlling stereochemistry of synthetic organic reactions. These boronic acids are found to recognize α and β-anomers of 2-deoxyribofuranosides. That is, when these boron compounds are added to a 1 : 1 mixture of α and β-t-butyl 5-O-benzyl-2-deoxy-D-ribofuranosides, the boronic acids 1 and 2 form the corresponding boronates preferentially with the β-anomer.
- Yamashita, Hiroshi,Amano, Koji,Shimada, Satoru,Narasaka, Koichi
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p. 537 - 538
(2007/10/03)
-
- CHEMISTRY OF NITRO ETHERS. XVIII. SIMPLIFIED SYNTHESIS OF 2-(4-NITROPHENYL)ETHANOL
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A method was developed for the preparative synthesis of 2-(4-nitrophenyl)ethanol by the nitration of 2-phenylethanol followed by acid hydrolysis of 2-(4-nitrophenyl)ethyl nitrate.
- Kochergin, P. M.,Blinova, L. S.
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p. 1556 - 1558
(2007/10/03)
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- Process for preparing 2-(o-aminophenyl)ethanol
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A process for preparing 2-(o-aminophenyl)ethanol comprising reducing 2-(o-nitrophenyl)ethanol with hydrogen in the presence of a Raney nickel catalyst is described, in which said reducing is carried out in the presence of a small amount of an alkali compound. The Raney nickel catalyst exhibits improved activity to achieve an increased reaction rate.
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- Electrogenerated Base (EG Base) Induced Hydroxymethylation of the Side Chain of Nitroalkylbenzenes with Paraformaldehyde
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Hydroxymethylation of nitroalkylbenzenes with paraformaldehyde was accomplished by electrolysis in a (CH2O)n-DMF-Et4NOTs-(Pt electrode) system.The reaction was found to be catalytic (0.25 faraday/mol) and dependent on the electroreduction of formaldehyde and/or nitroalkylbenzene.A variety of nitroalkylbenzenes were transformed to their corresponding mono- and/or bishydroxymethylated derivatives in good yield.The product yield and selectivity were shown to depend on the order of reagent addition, solvent, supporting electrolyte, and structure of the starting nitroalkylbenzenes.A plausible mechanism of the generation of base catalysts (EG base) in electroreductive media is discussed.
- Torii, Sigeru,Murakami, Yasuo,Tanaka, Hideo,Okamoto, Koichi
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p. 3143 - 3147
(2007/10/02)
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- Antibacterial Benzisoxazolones. An Unusual Rearrangement Product from o-Nitrostyrene Oxide en Route to the Photolabile Carbonyl Protecting Group (o-Nitrophenyl)ethylene Glycol
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In the process of synthesizing the known, photolabile protecting group (o-nitrophenyl)ethylene glycol, we uncovered an acid-mediated rearrangement of o-nitrostyrene oxide to 1-(hydroxymethyl)-2,1-benzisoxazol-3(1H)-one.The structure was ascertained by IR, UV, 1H NMR, 13C NMR, MS, and X-ray crystallography.Also the benzisoxazolone was prepared by independent synthesis from an o-nitrobenzoate.Another novel transformation uncovered was the conversion of o-nitrostyrene oxide to 2-(o-nitrophenyl)ethanol with use of potassium hydroxide and 18-crown-6.Similiar chemistry was insignificant with p-nitrostyrene oxide.The benzisoxazolone exhibited antibacterial and antileukemic activity (in vitro).
- Wierenga, Wendell,Harrison, Allen W.,Evans, Bruce R.,Chidester, Connie G.
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p. 438 - 442
(2007/10/02)
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- Process for the selective hydroxymethylation of nitrotoluenes
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The invention relates to a new process for the selective hydroxymethylation of substituted ortho- or paranitrotoluenes of the general formula (I) STR1 in order to prepare nitrophenylalkanols of the general formula (II) STR2 In the above formulae the nitro group is attached to the benzene ring in ortho or para position related to the methyl group or the hydroxyalkyl side chain, respectively, X stands for hydrogen, fluorine or an alkyl, alkoxy or nitro group, and n is 1, 2 or 3. According to the process of the invention the starting substance is hydroxymethylated with an excess of formaldehyde at a temperature above room temperature in dimethyl formamide and in the presence of a strong base. The reaction is performed in dimethyl formamide containing 0.1 to 1% by weight of water, and the reaction is directed to the formation of the required end-product by properly adjusting the temperature and the amount of formaldehyde and the base with respect to the starting compound of the general formula (I). In this way the required end-products can be prepared selectively also on an industrial scale.
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- Nucleotide. XIV. Substituierte β-Phenylaethyl-Gruppen. Neue Schutzgruppen fuer Oligonucleotid-Synthesen nach dem Phosphorsaeuretriester-Verfahren
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Various o- and p-substituted β-phenylethanols (2-10) have been synthesized and investigated as blocking groups in the phosphotriester approach.A large number of 5'-O-tritylated thymidine-3'-phosphotriesters (13-36) with two different phosphate protecting groups have been prepared, characterized, and studied according to their chemical stability and usefullness for oligonucleotide syntheses.The combination of a 5'-O-monomethoxytrityl- and a 3'-(2,5-dichlorophenyl, p-nitrophenylethyl)-phosphate function as in 18 turned out to possess optimal properties as a monomeric nucleotide building block due to the fact that these blocking groups can be quantitatively and selectively be removed without harming each other by trifluoroacetic acid in chloroform to 41, by oximate to 42, and by DBU to 43.The base-catalyzed removal of the monosubstituted phenylethyl groups by DBU or DBN respectively as well as the disubstituted phenylethyl groups by triethylamine in aprotic solvents is a β-elimination process leading to phosphodiesters without attack on the P-center.
- Uhlmann, Eugen,Pfleiderer, Wolfgang
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p. 1688 - 1703
(2007/10/02)
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- Process for the preparation of carbinols
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Organic compounds containing a carboxylic acid or carboxylic acid anhydride group are reduced when contacted with an alkali metal borohydride and a boron trihalide in a liquid medium in which diborane is soluble in the form of a labile borane adduct. Hydrolysis of the reaction mixture then provides a useful synthesis of the corresponding carbinols. The alkali metal borohydride-boron trihalide reagent may either be preformed and reacted subsequently with an organic compound containing a carboxylic acid or anhydride group, or the alkali metal borohydride-boron trihalide reagent may be produced in the presence of an organic compound containing a carboxylic acid or anhydride group. This development makes it possible to synthesize a wide variety of carbinols which are valuable and useful intermediates in organic synthesis.
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