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Communication | Special issue | Vol 30, No. 1, 1990, pp.253-256
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S19
Alkoxide-mediated Oxidative Ring Expansion of Benzocyclobutenes. A New Route to 3,4-Dihydroisocoumarines

Kozo Shishido, Kou Hiroya, Akitake Yamashita, Yuji Tokunaga, and Keiichiro Fukumoto*

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

Abstract

Sequential treatment of the dianion of 6 with a variety of esters (10) and MoO5·pyridine·HMPA complex provided the rearranged 2-hydroxy-1-indanones (7) along with the 1-acylbenzocyclobutenes (8), which were easily converted to 7. Transformation of 7 to the 3,4-dihydroisocoumarines (9) was achieved by oxidative cleavage followed by reduction and acid treatment.