657-83-0Relevant articles and documents
Arylsulfur chlorotetrafluorides as useful fluorinating agents: Deoxo- and dethioxo-fluorinations
Umemoto, Teruo,Singh, Rajendra P.
experimental part, p. 17 - 27 (2012/09/07)
Usage of arylsulfur chlorotetrafluorides 1 as versatile deoxo- and dethioxo-fluorinating agents is described. There have been developed two convenient methods for the in situ preparation of reactive arylsulfur trifluorides 2 from 1. The one is reduction of 1 with a reducer such as pyridine to 2, and the other is disproportionation of 1 with a diaryl disulfide to 2 with evolution of chlorine gas. The latter method is a convenient way to get neat 2 from 1. The in situ prepared 2 fluorinates many kinds of substrates such as alcohols, aldehydes, ketones, diketones, and carboxylic acids to give the corresponding CF, CF2, CF2CF2, and CF 3 compounds in high yields. 2 also fluorinates various sulfur compounds including CS groups to give CF2, OCF2, CF 3, and OCF3 compounds in high yields. Reactions of 2 with diols or bis(trimethylsilyl) derivatives of diols or amino alcohols provided the corresponding deoxofluoro-arylsulfinylation products in high yields. In addition, it has been found that chlorotetrafluorides 1 directly and effectively react with the sulfur compounds to give the corresponding fluoro compounds in high yields. Since they are the intermediates for the production of industrially useful arylsulfur pentafluorides, arylsulfur chlorotetrafluorides 1, in particular, phenylsulfur chlorotetrafluoride (1a) are expected to find use as inexpensive and versatile deoxo- and dethioxo-fluorinating agents for the preparation of many organofluoro compounds.
Oxidative fluorination of S, Se and Te compounds
Ou, Xiaobo,Janzen, Alexander F.
, p. 279 - 283 (2007/10/03)
The synthesis and mechanism of formation of cis- and trans-Ph2SF4 is described. Starting compounds are Ph2S or Ph2SF2 and the oxidizing agent is XeF2 in the presence of Et4NCl. Also described is the synthesis of related chalcogen(IV and VI) fluorides such as t-butylSF3, difluorodibenzothiophene, PhSeF3, Ph2SeF2, PhSF5, p-MeC6H4SF5, PhSeF5, and PhTeF5. The reactions of Ph2S(O)F2 with alcohols and with the H2O-HF-glass system are briefly described.
