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Communication | Special issue | Vol 5, No. 1, 1976, pp.413-418
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0413
Reactions of Stable Ylidic 1-Thianaphthalene with Electrrophiles. A New Ring Expansion Reaction

Mikio Hori,* Tadashi Kataoka, Hiroshi Shimizu, and Harumi Aoki

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

Reactions of 2-cyano-1-methyl-4-phenyl-1-thianaphthalene (1) with electrophiles, such as tetracyanoethylene, maleic anhydride, and 4-phenyl-1-thianaphthylium perchlorate gave the dimeric compound (II) of 1, but not any cycloaddition products. However, the treatment of 1 and dimethyl acetylenedicarboxylate afforded a new ring expansion product (III) having sulphur-containing nine-membered ring.