111698-34-1Relevant articles and documents
Sulfinate esters from methoxymethyl sulfides
Ko,Koo,Kim,Kim
, p. 2871 - 2876 (1995)
Several benzene (or phenylmethane) sulfinate esters were synthesized in 53-98% yields from the corresponding methoxymethyl (MOM) sulfides employing NBS as oxidant.
NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions
Zhang, Guofu,Fan, Qiankun,Wang, Huimin,Zhao, Yiyong,Ding, Chengrong
, p. 833 - 837 (2020/12/07)
We have developed a protocol for the NaHSO3-promoted esterification of sulfonyl hydrazides with alcohols for the synthesis of sulfinic esters. Various sulfonyl hydrazides could be converted to the corresponding sulfinic esters in good to high yields. The merits of this protocol include mild transition-metal-free reaction conditions, an inexpensive and available reagent, and operational simplicity. Controlled experiments reveal that this transformation probably undergoes via a radical pathway. (Figure presented.).
Direct synthesis of sulfinic esters via ultrasound accelerated tandem reaction of thiols and alcohols with N-bromosuccinimide
Nguyen, Lan-Anh Thi,Le, Tri-Nghia,Duong, Cong-Thang,Vo, Chi-Tam,Duus, Fritz,Luu, Thi Xuan Thi
, p. 519 - 528 (2021/05/27)
The direct transformation of various thiols and simple alcohols with N-bromosuccinimide into sulfinic esters has been investigated by using different categories of base/acidic catalysts as well as co-solvents under varied reaction conditions. The reaction was found out to afford the sulfinic esters with high yields in the absence of catalysts, especially within the shorter time under the acceleration of ultrasonic irradiation than under the longer-lasting conventional stirring conditions.
Metal- And oxidant-free electrochemical synthesis of sulfinic esters from thiols and alcohols
Ai, Chongren,Shen, Haiwei,Song, Dingguo,Li, Yujin,Yi, Xiao,Wang, Ze,Ling, Fei,Zhong, Weihui
supporting information, p. 5528 - 5531 (2019/10/22)
An efficient and eco-friendly electrochemical synthesis of various sulfinic esters from thiols and alcohols via sequential S-H/S bond cleavage and double S-O bond formation under mild reaction conditions has been developed. Stoichiometric oxidants, metal catalysts, activating agents and even added bases were avoided in this method, and the only by-product generated from this reaction was dihydrogen gas which could serve as a green source of energy. Various functional groups are compatible with this green protocol which can be easily conducted on a gram-scale.
Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates
Mampuys, Pieter,Zhu, Yanping,Sergeyev, Sergey,Ruijter, Eelco,Orru, Romano V. A.,Van Doorslaer, Sabine,Maes, Bert U. W.
supporting information, p. 2808 - 2811 (2016/07/06)
A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.
Tert-Butyl Sulfoxide as a Starting Point for the Synthesis of Sulfinyl Containing Compounds
Wei, Juhong,Sun, Zhihua
supporting information, p. 5396 - 5399 (2015/11/18)
Sulfoxides bearing a tert-butyl group can be activated using N-bromosuccinimide (NBS) under acidic conditions and then subsequently treated with a variety of nitrogen, carbon, or oxygen nucleophiles to afford a wide range of the corresponding sulfinic acid amides, new sulfoxides, and sulfinic acid esters.
The first effective procedure for the direct esterification and thiolysis of sulfinic acids
Drabowicz, Jozef,Kwiatkowska, Malgorzata,Kielbasinski, Piotr
experimental part, p. 3563 - 3564 (2009/06/18)
Alkyl arenesulfinates and S-thiosulfinates are readily accessible in good yields by the reaction of sulfinic acids and alcohols or thiols, respectively, in the presence of lanthanide(III) triflates as catalysts. Georg Thieme Verlag Stuttgart · New York.
Additive Pummerer reactions of vinylic sulfoxides. Synthesis of γ-hydroxy-α,β-unsaturated esters, α-hydroxyketones, and 2-phenylsulfenyl aldehydes and primary alcohols
Craig, Donald,Daniels, Kevin,MacKenzie, A. Roderick
, p. 11263 - 11304 (2007/10/02)
Treatment of β-monosubstituted vinylic sulfoxides 1 with trifluoroacetic anhydride in dichloromethane gave excellent yields of 1,2-bis(trifluoroacetoxy)thioethers 6. Mildly basic methanolysis of 2-alkyl-substituted 6 gave α-hydroxyaldehydes 11 as monomer-dimer mixtures; similar treatment of the 2-aryl analogues afforded aryl (hydroxymethyl) ketones 12. Compounds 11 underwent Wittig reactions with methoxycarbonylmethylenetriphenylphosphorane to give high yields of γ-hydroxy-α,β-unsaturated esters 13, predominantly as the E-isomers. β-Monosubstituted vinylic sulfoxides 1 possessing a β-aryl group, and β-disubstituted vinylic sulfoxides 3 reacted with trifluoromethanesulfonic anhydride-sodium acetate in acetic anhydride to give 2-(phenylsulfenyl) acylals 14. These gave 2-phenylsulfenyl aldehydes 15 upon basic methanolysis, and the corresponding primary alcohols 16 on reduction with sodium borohydride. Reaction of both geometric isomers of enantiomerically pure vinylic sulfoxide 1o with TFAA gave racemic 6o as a mixture of diastereomers. Reaction of optically pure (E)- and (Z)-1p with trifluoromethanesulfonic anhydride-sodium acetate in acetic anhydride gave acylal 19 in 10.5 and 23% e.e., respectively.
ORGANOSULPHUR COMPOUNDS XLVII ALKYLATION OF SULPHINIC ACIDS BY O-ALKYLISOUREAS: O-VERSUS S-REACTIVITY AND ASYMMETRIC SYNTHESIS OF ALKYL SULPHINATES
Kielbasinski, Piotr,Zurawinski, Remigiusz,Drabowitz, Jozef,Mikolajczyk, Marian
, p. 6687 - 6692 (2007/10/02)
The reaction of O-alkylisoureas with sulphinic acids was found to produce the corresponding sulphones and sulphinates, the latter being predominantly formed.The sulphinate to sulphone ratio is strongly influenced by the kind of alkyl groups in the O-alkylisourea and appeared to be also dependent on the solvent used.A few optically active sulphinates (e.e. up to 8.1percent) were prepared in the reaction between benzenesulphinic acid and a series of O-alkylisoureas bearing optically active substituents at the nitrogen atom.A possible reaction mechanism is discussed.
'One-Pot' Synthesis of Sulphinic Esters from Disulphides
Brownbridge, Peter,Jowett, Ian C.
, p. 252 - 254 (2007/10/02)
Alkane- and arenesulphinic esters can conveniently be prepared from disulphides and alcohols using N-bromosuccinimide or a combination of 3-chloroperoxybenzoic acid and N-bromosuccinimide.
