New consecutive photochemical reactions of naphtho[1,8-de]-1,3-dithiin-1-N-tosylsulfilimines via the through-space interaction between two sulfur atoms; A convenient method for preparation ofN-tosylaldimines

Abstract

Naphtho[1,8‐de]‐1,3‐dithiin‐1‐N‐tosylsulfilimines underwent facile consecutive photochemical reactions to give quantitatively the corresponding N‐tosylaldimines, together with naphtho[1,8‐cd]‐1,2‐dithiole, via a sulfur–sulfur interaction. The intermediate, 3‐hydro‐3‐phenyl‐naphtho[1,8‐ef][1,4]dithia[2]‐azepin, was isolated by liquid chromatography of the reaction mixtures, and its structure was determined by X‐ray crystallographic analysis. The proposed mechanism for these photochemical reactions is based on quantum yield measurements, photo‐intensity effects, and crossover experiments. © 1998 John Wiley & Sons, Inc. Heteroatom Chem 9:29–40, 1998