NEW CONSECUTIVE PHOTOCHEMICAL-REACTIONS OF NAPHTHO[1,8-DE]-1,3-DITHIIN-1-N-TOSYLSULFILIMINES VIA THE THROUGH-SPACE INTERACTION BETWEEN 2 SULFUR-ATOMS - A CONVENIENT METHOD FOR PREPARATION OF N-TOSYLALDIMINES

Naphtho[1,8-de]-1,3-dithiin-1-N-tosylsulfilimines underwent facile con secutive photochemical reactions to give quantitatively the correspond ing N-tosylaldimines, together with naphtho[1,8-cd]-1,2-dithiole, via a sulfur-sulfur interaction. The intermediate, ydro-3-phenyl-naphtho[1 ,8-e][1,4]dithia[2]-azepin, was isolated by liquid chromatography of t he reaction mixtures, and its structure was determined by X-ray crysta llographic analysis. The proposed mechanism for these photochemical re actions is based on quantum yield measurements, photo-intensity effect s, and crossover experiments. (C) 1998 John Wiley & Sons, Inc.