23730-26-9Relevant articles and documents
N - P -Toluenesulfinylimidazole: A New in situ Reagent for the Mild and Efficient Synthesis of p -Toluenesulfinate Alkyl Esters and Aryl Esters
Shaw, Jessica L.,Austermuehle, Brad J.,Witte, Jordan M.,Dorsey, Timothy R.,Delach, Christina,Hamaker, Christopher G.,Hitchcock, Shawn R.
supporting information, p. 2693 - 2701 (2021/04/27)
A new synthetic methodology has been developed for the synthesis of sulfinate alkyl and aryl esters. The methodology involves the combination of p -toluenesulfinic acid and 1,1′-carbonyldiimidazole (CDI) to create the putative reagent sulfinylimidazole. The process spontaneously releases carbon dioxide upon the addition of the CDI to the acid suggesting the rapid formation of the proposed reagent. Reaction of this reagent with a series of alcohols (primary, secondary, and tertiary) afforded the corresponding sulfinate alkyl esters in good to excellent yields by the addition of alcohols. It was also possible to form the related sulfinate aryl esters by treating the proposed sulfinylimidazole with selected phenols (phenol, p - tert -butylphenol, and thymol). The aryl esters were formed in excellent conversion based on analysis of the 500 MHz 1H NMR spectra of the crude reaction mixtures.
Metal-Free Electrophilic Alkynylation of Sulfenate Anions with Ethynylbenziodoxolone Reagents
Amos, Stephanie G. E.,Nicolai, Stefano,Gagnebin, Alec,Le Vaillant, Franck,Waser, Jerome
, p. 3687 - 3701 (2019/03/07)
Alkynyl sulfoxides are important building blocks with a unique reactivity in organic chemistry, but only a few reliable methods have been reported to synthesize them. A novel route to access alkynyl sulfoxides is reported herein by using ethynyl benziodoxolone (EBX) reagents to trap sulfenate anions generated in situ, via a retro-Michael reaction. The reaction takes place under metal-free and mild conditions. It is compatible with aryl, heteroaryl, and alkyl sulfoxides with up to 90% yield. This practical access to alkynyl sulfoxides is expected to facilitate the application of these useful building blocks in organic synthesis.
TBHP/TBAI-mediated oxidation of thiophenols for the synthesis of tert-butyl arylsulfinates
Wen, Chunxiao,Wu, Jiawei,Ou, Yingcong,Huang, Yulin,Zhang, Kun,Chen, Qian
supporting information, p. 3609 - 3611 (2018/09/13)
A novel and efficient TBHP/TBAI-mediated oxidation of thiophenols is described. The reactions proceeded smoothly to give tert-butyl arylsulfinates in up to 82% yield with good functional group compatibility under mild conditions.