Barton-Kellogg Olefination of (CF₃S)₂C=S and Subsequent Cyclopropanation for the Installation of Bulky Bis(trifluoromethylthio)methylene Group.

ABSTRACT: A protocol was developed for the large-scale preparation (nearly 200 g per batch) of (CF₃S)₂C=S. The synthesis of gem-bis(trifluoromethylthio)alkenes was achieved through the Barton-Kellogg reaction, without the involvement of trivalent phosphines. With slight modifications to the reaction conditions, the synthesis of gem-bis(trifluoromethylthio)cyclopropanes, which are difficult to obtain by other methods, can be realized. Due to the large steric hindrance of the trifluoromethylthio group, the CF₃S group may be positioned close to the trans-substituent rather than the cis-substituent in cyclopropanes, as confirmed by single-crystal X-ray analysis, contributing to unique NMR structural characteristics. Further investigation into

SUBMITTER: Sun J 

PROVIDER: S-EPMC11862935 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature