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 of N-tosylaldimines

✍ Scribed by Takayoshi Fujii; Ernst Horn; Naomichi Furukawa

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 259 KB
• Volume: 9
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1998)9:1<29::aid-hc4>3.0.co;2-y

✦ Synopsis

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.