REACTION OF AMINOSULFUR TRIFLUORIDES WITH ALCOHOLS - INVERSION VS RETENTION

Reaction of aminosulfur trifluorides with alcohols replaces the hydrox y group with fluorine. A study with the cyclic secondary alcohols tran s-2-bromoindan-1-ol (3), trans-2-methylcyclopentanol (7), cis-2-methyl cyclopentanol (8), trans-[2-H-2(1)]cyclopentanol (9), cis-[2-H-2(1)]cy clopentanol (10) and trans-2-fluorocyclopentanol (11) gave primarily i nversion of configuration via an S(N)1-like pathway, The product stere ochemistry and alkene formation in the reaction of aminosulfur trifluo rides with cyclopentanols was similar to the products of solvolysis of cyclopentyl tosylates' in methanol. The stereochemistry of the fluoro products was confirmed by independent synthesis or assigned by H-1 an d F-19 NMR spectral data except for the deuteriated products 14 and 15 whose stereochemistry was assigned by their H-2 NMR data.