Unusual Reaction of Epoxynorbornane with Trifluoromethylsulfenyl Chloride

Abstract

The treatment of 1, 2-exo-epoxynorbornane ( 1 ) with (trifluororomethyl)sulfenyl chloride ( 2 ) in dry pentane at −80^ˆC furnishes 16 compounds. Of which, 7 are derived from the reaction of the solvent with 2 , 7 others are formed from the substrate ( 1 ) and the remaining two arise from the reagent ( 2 ) itself. The probable mechanism of their formation and their mass spectral characterization are presented in this paper.

Keywords:

• Auto-catalysis;
• epoxide ring opening;
• free radical reactions;
• solvent-derived products