- Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis
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The synthesis of anilines and indoles from cyclohexanones using a Pd/C-ethylene system is reported. A simple combination of NH4OAc and K2CO3 under nonaerobic conditions was found to be the most suitable to perform this reaction. Hydrogen transfer between cyclohexanone and ethylene generates the desired products. The reaction tolerates a variety of substitutions on the starting cyclohexanones.
- Maeda, Katsumi,Matsubara, Ryosuke,Hayashi, Masahiko
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supporting information
p. 1530 - 1534
(2021/03/08)
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- Photoredox-Catalyzed Generation of Acetonyl Radical in Flow: Theoretical Investigation and Synthetic Applications
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A hydrogen atom transfer (HAT) step from acetone allowed the smooth generation of acetonyl radical that was then exploited as synthon in the mild formation of C-C bonds under flow conditions. The process was promoted by aryl radicals photocatalytically generated via single-electron transfer (SET) reduction of arenediazonium salts. The mechanism has been investigated by a combined experimental and computational approach and further supported by deuterium labeling experiments.
- Anselmo, Manuel,Basso, Andrea,Protti, Stefano,Ravelli, Davide
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p. 2493 - 2500
(2019/03/08)
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- Intramolecular Schmidt Reaction of Vinyl Azides with Cyclic Ketones
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Cyclic ketones tethered with a vinyl azide group undergo a Schmidt-hydrolysis sequence to give secondary lactams bearing a ketone side chain. Secondary lactams are obtained in a regioselective manner that is not possible in a conventional Schimdt reaction. In addition to the well-documented C-2 nucleophilicity, the N nucleophilicity of vinyl azide disclosed in this work opens a new direction for reaction invention involving vinyl azides.
- Chen, Peng,Sun, Chu-Han,Wang, Yu,Xue, Ying,Chen, Chen,Shen, Mei-Hua,Xu, Hua-Dong
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p. 1643 - 1646
(2018/03/23)
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- Structure-activity relationships (SAR) and structure-kinetic relationships (SKR) of sulphone-based CRTh2 antagonists
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Monocyclic and bicyclic ring systems were investigated as the "core" section of a series of diphenylsulphone-containing acetic acid CRTh2 receptor antagonists. A range of potencies were observed and single-digit nanomolar potencies were obtained in both the monocyclic and bicyclic cores. Residence times for the monocyclic compounds were very short. Some of the bicyclic cores displayed better residence times. A methyl group in the northern part of the core, between the head and tail was a necessary requirement for the beginnings of long residence times. Variations of the tail substitution maximised potencies and residence times.
- Buil, Maria Antonia,Calbet, Marta,Castillo, Marcos,Castro, Jordi,Esteve, Cristina,Ferrer, Manel,Forns, Pilar,González, Jacob,López, Sara,Roberts, Richard S.,Sevilla, Sara,Vidal, Bernat,Vidal, Laura,Vilaseca, Pere
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p. 102 - 133
(2016/03/04)
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- CANNABINOID AGONISTS
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The present disclosure relates to compounds useful as agonists of the cannabinoid receptors. The disclosure also provides pharmaceutically acceptable compositions comprising the compounds of the disclosure and methods of using the compositions in the treatment of various disorders, either alone or in combination therapy. The compounds of the invention have Formula (I).
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Page/Page column 73
(2011/09/15)
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- CRTH2 MODULATORS
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Modulators of CRTH2, particularly antagonists of CRTH2, that are useful for treating various disorders, including asthma and respiratory disorders are disclosed. The compounds fall within a genus described by formula I
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-
Page/Page column 96-97
(2010/04/27)
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- TETRAHYDROINDOLE DERIVATIVES AS NADPH OXIDASE INHIBITORS
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The present invention is related to tetrahydroindolederivatives of Formula (I), pharmaceutical composition thereof, methods of preparation thereofand to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphateoxidase (NADPH Oxidase).
- -
-
Page/Page column 50
(2008/12/04)
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- Oxidative conversion of α,α-disubstituted acetamides to corresponding one-carbon-shorter ketones using hypervalent iodine (λ5) reagents in combination with tetraethylammonium bromide
-
(Chemical Equation Presented) α,α-Disubstituted acetamides undergo oxidative dehomologation to give one-carbon-shorter ketones when reacted with a hypervalent iodine (λ5) reagent in combination with tetraethylammonium bromide (TEAB) in various solvents. In further studies, one such combination of a hypervalent iodine (λ5) reagent, o-iodoxybenzoic acid, and TEAB has been established as a new, mild, efficient, and general method for the transformation.
- Bellale, Eknath V.,Bhalerao, Dinesh S.,Akamanchi, Krishnacharya G.
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supporting information; experimental part
p. 9473 - 9475
(2009/04/06)
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- Convenient and efficient Pd-catalyzed regioselective oxyfunctionalization of terminal olefins by using molecular oxygen as sole reoxidant
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(Chemical Equation Presented) Just the one: The combination of palladium dichloride and N,N-dimethylacetamide (DMA) constitutes a highly efficient and reusable catalytic system, which uses molecular oxygen as the sole reoxidant for liquid-phase Wacker oxidation and acetoxylation of terminal olefins to the corresponding methyl ketones and linear allylic acetates, respectively (see scheme). 2006 Wiley-VCH Verlag GmbH Co. KGaA.
- Mitsudome, Takato,Umetani, Takuya,Nosaka, Naoya,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
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p. 481 - 485
(2007/10/03)
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- Highly efficient Wacker oxidation catalyzed by heterogeneous Pd montmorillonite under acid-free conditions
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Palladium-montmorillonite was proven to be highly efficient for the Wacker oxidation of terminal olefins to the corresponding methyl ketones. The catalyst was reusable while maintaining high activity and selectivity.
- Mitsudome, Takato,Umetani, Takuya,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
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p. 1425 - 1428
(2007/10/03)
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- A radical cyclisation based cyclopentenone annulation of allyl alcohols
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A four-step cyclopentenone annulation reaction of allylic alcohols employing a 5-exo-trig radical cyclisation reaction of mixed allyl methyl ketals of bromoacetone as the key step is described. The annulated product 12b obtained from 2,3-dimethylcyclohexenol has been further elaborated into (±)-epibakkenolides employing a 5-exo-dig radical cylisation reaction based α-spiro-β-methylene-γ-butyrolactone annulation methodology.
- Srikrishna,Viswajanani,Sattigeri
-
p. 2975 - 2983
(2007/10/03)
-
- Cross-coupling reaction of α-chloroketones and organotin enolates catalyzed by zinc halides for synthesis of γ-diketones
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The reaction of tin enolates 1 with α-chloro- or bromoketones 2 gave γ-diketones (1,4-diketones) 3 catalyzed by zinc halides. In contrast to the exclusive formation of 1,4-diketones 3 under catalytic conditions, uncatalyzed reaction of 1 with 2 gave aldol-type products 4 through carbonyl attack. NMR study indicates that the catalyzed reaction includes precondensation between tin enolates and α-haloketones providing an aldol-type species and their rearrangement of the oxoalkyl group with leaving halogen to produce 1,4-diketones. The catalyst, zinc halides, plays an important role in each step. The carbonyl attack for precondensation is accelerated by the catalyst as Lewis acid and the intermediate zincate promotes the rearrangement by releasing oxygen and bonding with halogen. Various types of tin enolates and α-chloro and bromoketones were applied to the zinc-catalyzed cross-coupling. On the other hand, the allylic halides, which have no carbonyl moiety, were inert to the zinc-catalyzed coupling with tin enolates. The copper halides showed high catalytic activity for the coupling between tin enolates 1 and organic halides 7 to give γ,δ-unsaturated ketones 8 and/or 9. The reaction with even chlorides proceeded effectively by the catalytic system.
- Yasuda, Makoto,Tsuji, Shoki,Shigeyoshi, Yusuke,Baba, Akio
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p. 7440 - 7447
(2007/10/03)
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- Palladium(II)-catalyzed oxidation of terminal alkenes to methyl ketones using molecular oxygen
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Palladium(II) acetate catalyzes the aerobic oxidation of terminal alkenes in toluene into the corresponding methyl ketones in the presence of a catalytic amount of pyridine using propan-2-ol as a reductant and molecular oxygen as an oxidant. Two catalytic cycles sharing a Pd(II)-OOH species are proposed. One is the formation of a Pd(II)-H species in the oxidation of propan-2-ol to acetone, followed by reaction with molecular oxygen to give a Pd(II)-OOH species, and the other is peroxypalladation of an alkene with the Pd(II)-OOH species produced to afford a methyl ketone in the presence of H2O2 produced by the former catalytic cycle. The Royal Society of Chemistry 2000.
- Nishimura, Takahiro,Kakiuchi, Nobuyuki,Onoue, Tomoaki,Ohe, Kouichi,Ucmura, Sakae
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p. 1915 - 1918
(2007/10/03)
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- A synthetic approach to perhydro-3-isoquinolinones bearing an angular methyl group via organocuprate addition
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The addition of organocuprates to the activated C-C double bond in 2H-3,3a,4,5,6,7-hexahydro-2-indenone followed by trapping of the anionic intermediate with Mel as electrophile is reported. Structural assignment of the resulting product was carried out v
- Stanetty, Peter,Bahardoust, M. Hassan,Mihovilovic, Marko D.,Mereiter, Kurt
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p. 1257 - 1268
(2007/10/03)
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- Convenient Wacker oxidations with substoichiometric cupric acetate
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A modification of the Wacker oxidation of terminal olefins to methyl ketones using substoichiometric amounts of Cu(OAc)2 as a redox shuttle reagent is described. The modified procedure is generally high yielding despite reduced levels of copper salt and convenient. Importantly, in a problematic case, the conditions suppressed acidic hydrolysis during oxidation of substrate (+)-5 containing an acetonide.
- Smith III, Amos B.,Cho, Young Shin,Friestad, Gregory K.
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p. 8765 - 8768
(2007/10/03)
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- Cyclopentaannulation of Allyl Alcohols via a Radical Cyclisation Reaction. Total Synthesis of 4-Epibakkenolide-A
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A four step cyclopentaannulation methodology starting from allyl alcohols using 5-exo-trig radical cyclisation as the key reaction, and its application to the total synthesis of 4-epibakkenolide is described.
- Srikrishna, A.,Viswajanani, R.,Sattigeri, J. A.
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p. 469 - 470
(2007/10/02)
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- Three-Component Radical Condensations Involving Benzoylmethyl Radicals, Alkenes, and Diphenyl Disulfide
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Acyl-substituted methyl radicals (RCOCH2.; R = H, Me, Ph), generated by photolysis of RCOCH2HgCl, add to alkenes, enol ethers, or vinyl sulfides to give adduct radicals that are readily trapped by PhSSPh to yield a three-component condensation product.The presence of an alkali metal carbonate is crucial in preventing side reactions resulting in the conversion of the mercurial to RCOCH3 by PhSH formed in the photolysis.
- Russell, Glen A.,Kulkarni, Shekhar V.
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p. 2678 - 2685
(2007/10/02)
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- A NEW SYNTHETHIC ASPECT OF ACETIC NITRONIC ANHYDRIDES
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A facile and convenient synthesis of acetic nitronic anhydrides from aliphatic nitroalkenes and lithium ketone enolates and the efficient conversion of these anhydrides to 1,4-diketones, alkylpyrroles, diketone monooximes, dihydro-1,2-oxazines, pyrrolidin
- Miyashita, Masaaki,Awen, Bahlul Z. E.,Yoshikoshi, Akira
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p. 7569 - 7586
(2007/10/02)
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- Hard acid and soft nucleophile systems. Part 12. Regioselective functionalization of 1,3-dienes through the Lewis acid mediated thienium cation Diels-Alder reaction
-
Reaction of α-Ethylthio-β-nitroolefms with 1,3-dienes under acidic Diels-Alder conditions afforded Z-olefins through stereoselective 1,4- functionalization.
- Fuji, Kaoru,Khanapure, Subhash P.,Node, Manabu,Kawabata, Takeo,Itoh, Akichika,Masaki, Yukio
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p. 7393 - 7402
(2007/10/02)
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- Multistep electron transfer in palladium-catalyzed aerobic oxidations via a metal macrocycle-quinone system
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Selective palladium-catalyzed aerobic conditions of olefins and conjugated dienes with the aid of a metal macrocycle-quinone system have been developed. This involves a multistep electron transfer with three catalysts (Pd(OAc)2, hydroquinone, metal macrocycle). The triple catalytic system was applied to (i) 1 ,4-oxidation of conjugated dienes (1,4-diacetoxylation and 1,4-dialkoxylation), (ii) oxidation of terminal olefins to ketones, and (iii) allylic oxidation of cyclic olefins to 2-alken-1-yl acetates. The reactions occur under very mild conditions, (i) and (ii) at room temperature and (iii) at 60 °C, and are reminiscent of aerobic processes occurring in living organisms. Thus, there is an electron transfer from the substrate to Pd(II) giving Pd(0), followed by another electron transfer from Pd(0) to benzoquinone. The hydroquinone thus formed transfers electrons to the oxidized form of the metal macrocycle, which is reduced. The latter is reoxidized by electron transfer to molecular oxygen. A number of metal macrocycles such as metal(salen) complexes Co(salophen), Co(TPP), and iron phthalocyanine (Fe(Pc)) were tested as oxygen-activating complexes. In the 1,4-diacetoxylation of 1,3-dienes, and in the allylic oxidation, several of these metal macrocycles gave good results. In the 1,4-dialkoxylation of 1,3-dienes and in the oxidation of terminal olefins to ketones, which occur in the presence of a strong acid, only Fe(Pc) survived the reaction conditions.
- B?ckvall, Jan-E.,Hopkins, R. Bruce,Grennberg, Helena,Mader, Mary M.,Awasthi, Alok K.
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p. 5160 - 5166
(2007/10/02)
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- One-Pot Synthesis of 1,4-Diketones from Nitroalkenes and Ketones
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A convenient one-pot synthesis of 1,4-diketones was achieved by the conjugate addition of lithium enolates of ketones to nitroalkenes, followed by in situ hydrolysis of the resulting lithium salts of aci-nitro compounds with aqueous hydrochloric acid in tetrahydrofuran.
- Miyashita, Masaaki,Awen, Bahlul Z. E.,Yoshikoshi, Akira
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p. 563 - 564
(2007/10/02)
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- RADICAL REACTION OF ACETONYLTRIBUTYLSTANNANE WITH α-(PHENYLSELENO)CARBONYL COMPOUNDS: A NOVEL PROCEDURE FOR PREPARATION OF 1,4-DICARBONYL COMPOUNDS
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Radical reaction of acetonyltributylstannane 1 with α-(phenylseleno)carbonyl compounds 2 gave 1,4-dicarbonyl compounds in high yield.The SH2' mechanism via the stannyl enolate in equilibrium with acetonylstannane is postulated.
- Watanabe, Yoshihiko,Yoneda, Tetsuo,Ueno, Yoshio,Toru, Takeshi
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p. 6669 - 6672
(2007/10/02)
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- SYNTHESIS OF UNSYMMETRICAL 1,4-DIKETONES BY THE CERIC AMMONIUM NITRATE PROMOTED CROSS-COUPLING OF TRIMETHYLSILYL ENOL ETHERS
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Unsymmetrical 1,4-diketones are prepared in good yields (60-80percent) by cerium (IV) ammonium nitrate oxidative cross-coupling between 1,2-disubstituted and 1-substituted trimethylsilyl enol ethers.
- Baciocchi, Enrico,Casu, Angela,Ruzziconi, Renzo
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p. 3707 - 3710
(2007/10/02)
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- MULTI-STEP CATALYSIS FOR THE OXIDATION OF OLEFINS TO KETONES BY MOLECULAR OXYGEN IN CHLORIDE FREE MEDIA
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A multi-step catalytic system consisting of Pd(II)/Pd(0) - benzoquinone/hydroquinone - Fe(Pc)ox/Fe(Pc) was utilized to achieve a mild and selective aerobic oxidation of terminal olefins to methyl ketones in chloride free media.
- Baeckvall, Jan-E.,Hopkins, R. Bruce
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p. 2885 - 2888
(2007/10/02)
-
- THE SYNTHESIS AND CHEMISTRY OF AZOLENINES. PART 12. ISOLATION OF INTERMEDIATE 2-HYDROXY-3,4-DIHYDRO-2H-PYRROLES IN THE PAAL-KNORR 1H-PYRROLE SYNTHESIS.
-
Treatment of 1,4-diketones with liquid ammonia gives high yields of isolable 2-hydroxy-3,4-dihydro-2H-pyrrole intermediates.These intermediates, which do not appear to have been observed previously in the Paal-Knorr synthesis with ammonia, have been fully characterized by i.r. and 1H and 13C n.m.r. spectroscopy; in most cases they decompose quantitatively into 1H-pyrroles on standing.The intermediate from hexane-2,4-dione may also be prepared using concentrated aqueous ammonia.
- Chiu, Pak-Kan,Sammes, Michael P.
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p. 3531 - 3538
(2007/10/02)
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- 2-Ethoxy-2-propenyl Diethyl Phosphate. An Efficient Halo Acetone Equivalent for the Pd-Catalyzed Cross-coupling with Tin Enolates
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In the presence of Pd(0) complexes, 2-ethoxy-2-propenyl diethyl phosphate was found to react with organotins to give the corresponding coupling products, showing to be a more efficient halo acetone equivalent compared with the corresponding acetate or carbonate.Reaction with tin enolates gave the 1,4-diketone in moderate to good yields.
- Kosugi, Masanori,Ohashi, Kenji,Akuzawa, Kazuko,Kawazoe, Takashi,Sano, Hiroshi,Migita, Toshihoko
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p. 1237 - 1238
(2007/10/02)
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- SYNTHESIS OF 1,4-DICARBONYL COMPOUNDS BY THE CERIC AMMONIUM NITRATE PROMOTED REACTION OF KETONES WITH VINYL AND ISOPROPENYL ACETATE
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1,4-Diketones and 4-ketoaldehydes dimethylacetals can be prepared in good yields (65-82percent) by the cerium(IV) ammonium nitrate promoted reaction of ketones with isopropenyl acetate and vinyl acetate, respectively.
- Baciocchi, Enrico,Civitarese, Giampiero,Ruzziconi, Renzo
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p. 5357 - 5360
(2007/10/02)
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- REGIOSELECTIVE HYDRATION OF ALKYNONES BY PALLADIUM CATALYSIS
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Diketones are regioselectively prepared from alkynyl ketones under mild conditions by palladium catalysis; 5-heptyn-2-one and 2-(2-nonynyl)cyclohexanone give 1,4-diketones whereas 2-(2-heptynyl)cyclopentanone and 5,6-didehydroprostaglandin E2 methyl ester afford 1,5-diketones.
- Imi, Katsuharu,Imai, Kumiko,Utimoto, Kiitiro
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p. 3127 - 3130
(2007/10/02)
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- A NEW REAGENT FOR A "ONE-POT" CYCLOPENTENONE ANNELATION
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A new reagent, 3-chloro-2-diethylphosphoryloxy-1-propene (2), for the preparation of cyclopentenones from ketone precursors via a "one-pot" synthesis is described.
- Welch, S. C.,Assercq, J.-M.,Loh, J.-P.
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p. 1115 - 1118
(2007/10/02)
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- One-pot Synthesis of 2-Substituted Cyclohexanones
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The one-pot synthesis of 2-substituted cyclohexanones involves alkylation of 2-hydroxymethylenecyclohexanone (1) in the presence of solid KOH
- Ravikumar, V. T.,Sathyamoorthi, G.,Thangaraj, K.,Rajagopalan, K.
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- MICHAEL REACTION OF SILYL ENOL ETHERS OR KETENE SILYL ACETALS WITH CONJUGATED NITRO OLEFINS ACTIVATED BY THE LEWIS ACID: NEW SYNTHESIS OF 1,4-DIKETONES AND gamma -KETO ESTERS.
-
New one-pot procedures for the synthesis of 1,4-diketones and gamma -keto esters utilizing conjugated nitro olefins are described. Reaction of silyl enol ethers with aliphatic nitro olefins in the presence of a Lewis acid affords 1,4-diketones in good yie
- Miyashita,Yanami,Kumazawa,Yoshikoshi
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p. 2149 - 2156
(2007/10/02)
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- DECOMPOSITION DU PERCARBONATE DE O,O-t-BUTYLE ET O-ISOPROPENYLE EN SOLUTION-2. ACETONYLATION DE CYCLANONES ET OXACYCLANES.
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The decomposition of O,O-tert-butyl and O-isopropenyl peroxycarbonate in cyclanones and oxycyclanes leads to acetonylated derivatives of these solvents.Although the reaction mechanism involves in both cases the addition of free radicals derived from solvent to the double bond of the peroxycarbonate, the orientation of the whole process depends on the solvent.In the case of oxacyclanes the relative ratios of α-,β-and γ-(with regard to the heteroatom) acetonylated products are likely to express the reactivity of t-butoxy radicals towards the differenet carbon atoms of the solvent.On the contrary, in the case of cyclanones transfer reactions occur from β- or γ-radicals (with regard to the carbonyl group) to α-carbon atoms of other solvent molecules and the relative ratios of α-, β- and γ-acetonylated products depend on on the peroxycarbonate concentration: when it is high, about 25percent β and γ isomers are formed; when it is low, only the α isomer is obtained.
- Jaouhari, R.,Maillard, B.,Filliatre, C.,Villenave, J. J.
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p. 1559 - 1566
(2007/10/02)
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- Reactions radicalaires du percarbonate de O,O-tert-butyle et O-isopropenyle: acetonylations assistees par un co-amorceur
-
By decomposition in alkanes, ethers, ketones, acids, esters and nitriles of equimolecular mixtures of O,O-tert-butyl and O-isopropenyl peroxicarbonate and tert-butyl peroxyacetate, the "assisted" acetonylation of the solvents has been accomplished.The presence of the co-initiator allows the yield of the free radical acetonylation to be markedly improved: the formation of the by-product acetonylacetone is avoided and the yield of acetonylated derivatives is strongly enhanced while the regioselectivity of the processes is preserved and even increased in some cases.
- Jaouhari, Rabih,Filliatre, Claude,Villenave, Jean-Jacques
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p. 2295 - 2298
(2007/10/02)
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- 3-Chloro-2-(trimethylsiloxy)-1-propene as an Electrophilic Acetonyl Equivalent. A Novel Regioselective Synthesis of 1,4-Dicarbonyl Compounds
-
α-Metalated imines, hydrazones, and activated methylene compounds are acetonylated with 3-chloro-2-(trimethylsiloxy)-1-propene in high yield.Highly regioselective acetonylation at either the tertiary or secondary α-carbon of 2-methylcyclohexanone can be carried out by selecting the reaction conditions.
- Hosomi, Akira,Shirahata, Akihiko,Araki, Yoshitaka,Sakurai, Hideki
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p. 4631 - 4633
(2007/10/02)
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- Convenient Synthesis of Jasmonoid Compounds from γ-(Trimethylsiloxy)butyronitrile
-
1,4-Dioxygenated compounds 4 are constructed by the addition of a Grignard reagent to γ-(trimethylsiloxy)nitriles 1,2, and 3 and subsequent hydrolysis.Oxidation of 4 with pyridinium chlorochromate or Jones reagent yields compounds 5 which are used to produce cyclopentenones 6.Methyl jasmonate and methyl dihydrojasmonate are made by the conjugate addition of silylated ketene acetal 9 to 6a and 6b, respectively, and subsequent protodesilylation. γ-Jasmolactone is also derived from 4a by oxidation with pyridinium dichromate in DMF followed by reduction with NaBH4 in ethanol.
- Matsuda, Isamu,Murata, Shizuaki,Izumi, Yusuke
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p. 237 - 240
(2007/10/02)
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- Selective reactions of free radicals with olefins in the presence of an ion of Mn, V, or Ce
-
An olefin is reacted with a source of X free radical in the presence of an ion of manganese, vanadium, or cerium having a valence higher than the lowest valence above the zero valent form of the metal to form derivatives of the olefin that contain one or more functional groups. The free radical X is one that is resistant to substantial oxidation by the ion of the metal and is obtained from ketones, aldehydes, esters, nitriles, nitroparaffins, sulfoxides, thiosulfonic acid esters, alkanesulfonic acids, alkanesulfinic acids, and thiols.
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