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Communication | Special issue | Vol 8, No. 1, 1977, pp.109-114
Published online, 1st January, 1970
DOI: 10.3987/S(S)-1977-01-0109
Reaction of Diophenylketene with Conjugated Sulfilimines

Yoshio Tomimatsu,* Kanako Satoh, and Masanori Sakamoto

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

Cycloaddition reactions of diphenylketene (I) with N-pyridin-2-yl-S,S-dimethylsulfilimine (II), N-benzoxazol-2-yl-S,S-dimethylsulfilimine (IV), and N-benzthiazol-2-yl-S,S-dimethylsulfilimine (VI) were investigated. I reacted with II, IV, and VI giving cycloadducts, 2,3-dihydro-3-keto-2,2-diphenylimidazo[1,2-a]pyridine (IIIa), 2,3-dihydro-3-keto-2,2-diphenylimidazo[2,1-b]benzoxazole (V), and 2,3-dihydro-3-keto-2,2-diphenylimidazo[2,1-b]benzthiazole (VII) by accompanying an elimination of dimethyl sulfide, respectively.
On the other hand, N-benzimidoyl-S,S-dimethylsulfilimine (VIII), contrary to our expectation, was not cyclized, but gave a Michael type adduct (IX).