41103-87-1Relevant articles and documents
Br?nsted acid-catalyzed chemodivergent reactions of: Ortho -mercaptobenzyl alcohols with 3-alkyl-2-vinylindoles and styrenes: [5+2] cyclization versus hydroxysulfenylation
Zhao, Jia-Jia,Tang, Man,Zhang, Hong-Hao,Xu, Meng-Meng,Shi, Feng
, p. 5953 - 5956 (2016)
Chemodivergent [5+2] cyclization and hydroxysulfenylation reactions of ortho-mercaptobenzyl alcohols with 3-alkyl-2-vinylindoles and styrenes were established in the presence of Br?nsted acid, which provide efficient methods for constructing benzoxathiepi
Solvent-enabled radical selectivities: Controlled syntheses of sulfoxides and sulfides
Wang, Huamin,Lu, Qingquan,Qian, Chaohang,Liu, Chao,Liu, Wei,Chen, Kai,Lei, Aiwen
supporting information, p. 1094 - 1097 (2016/01/20)
Controlling selectivity is of central importance to radical chemistry. However, the highly reactive and unstable radical intermediates make this task especially challenging. Herein, a strategy for taming radical redox reactions has been developed, in which solvent-bonding can alter the reactivity of the generated radical intermediates and thereby drastically alter the reaction selectivity at room temperature. Various β-oxy sulfoxides and β-hydroxy sulfides can be facilely obtained, some of which are difficult to synthesize by existing methods. Notably, neither a metal catalyst nor any further additives are necessary in these processes. Solvent selection alters the reactivity of the generated reaction intermediate and drastically switches the reaction selectivity under simple and mild conditions. Various β-oxy sulfoxides and β-hydroxy sulfides could be facilely obtained from readily available starting materials. Importantly, neither a metal catalyst nor an additional additive was necessary in these transformations.
A novel sulfinylation of alkenes by tosyl cyanide with titanium(IV) chloride
Morgan, Paul E.,McCague, Ray,Whiting, Andrew
, p. 4857 - 4860 (2007/10/03)
Tosyl cyanide is activated by titanium(IV) chloride to generate a tolylsulfinyl chloride equivalent, which readily stereo- and regio- specifically adds to certain alkenes to provide β-chlorosulfoxides. These chlorides rapidly hydrolyse on silica gel to provide β-hydroxysulfoxides in stereocontrolled manner.