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Communication | Regular issue | Vol 26, No. 9, 1987, pp.2361-2364
Published online, 1st January, 1970
DOI: 10.3987/R-1987-09-2361
Competitive Electrocyclic Reaction of o-Quinodimethane: Sequential Electrocyclic-double[3,3]sigmatropic Reactions for the Construction of 4-Alkylideneisochroman-3-ones

Kozo Shishido, Hironori Komatsu, Keiichiro Fukumoto, and Tetsuji Kametani

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Thermolysis of allyl 1-alkenylbenzocyclobutenyl-1-carboxylate (5a-f) produced a mixture of 4,4-disubstituted isochroman-3-ones (6a-f), dihydronaphthalenes (8a-f), and 4-alkylideneisochroman-3-ones (7a-f) in good yield. The third product (7a-f) was generated via an unprecedented sequential electrocyclic-double[3,3]sigmatropic reactions of Z-o-quinodimethane.