Conformational analysis and photochemical behavior of sulfoxides in the naphtho[1,2-b]thiopyran and naphtho[2,1-b]thiopyran series

Abstract

The sulfoxides derived from 2,3-dihydro-4H-naphtho[1,2-b]thiopyran and its 4-phenyl and 4-oxo derivatives, as well as the analogous sulfoxides in the 2,3-dihydro-1H-naphtho[2,1-b]thiopyran series, have been synthesized and their structures established by spectroscopic methods, especially 1H and 13C nmr. On photolysis these sulfoxides have been found to react by a rather inefficient photochemical deoxygenation pathway.