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Communication | Regular issue | Vol 38, No. 9, 1994, pp.1975-1978
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6835
Synthesis of Strained 8-Membered Heterocyclic Allenes by [3,3] Sigmatropic Rearrangement and Their Reactivities

Shinya Harusawa, Hideki Moriyama, Hirofumi Ohishi, Ryuji Yoneda, and Takushi Kurihara*

*Faculty of Pharmaceutical Science, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan


A new type of 8-membered heterocyclic allenes were synthesized by the [3,3] sigmatropic ring expansion of 6-membered cyclic thionocarbonates. The MNDO optimized structure indicated the allenyl moiety in cyclic allene (3) is bent and strained. Reactivities of the heterocyclic allenes were also examined.