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Communication | Regular issue | Vol 16, No. 12, 1981, pp.2085-2090
Published online, 1st January, 1970
DOI: 10.3987/R-1981-12-2085
Diels-Alder Type Reactions of 2-Phenyl-1-azaspiro[2.2]pent-1-ene

Otohiko Tsuge,* Toshiyuki Ohnishi, and Hiroyuki Watanabe

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan

Abstract

Highly strained 2-phenyl-1-azaspiro[2.2]pent-1-ene reacted with cyclopentadienones to give the corresponding 2H-azepine-2-spiro-cyclopropanes directly, with loss of carbon monoxide. However, the reaction of the azaspiropentene with 1,3-diphenylisobenzofuran afforded the exo-Diels-Alder adduct. The azaspiropentene reacted with thiobenzoyl isocyanates to give 3-aryl-5-oxo-2,4,6-thiadiazabicyclo[5.2.0]nona-3,6-dienes arising from the rearrangement of initial [4 + 2] cycloadducts.