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Communication | Regular issue | Vol 31, No. 9, 1990, pp.1589-1592
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5502
Accentuation of the Di-π-Methane Reactivity by Central Carbon Substitution in the 4-(Phenylmethyl)-2(5H)-furanone System

Osamu Muraoka,* Genzoh Tanabe, and Takefumi Momose*

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama 930-01, Japan


The effect of ’central methane’ substitution on the di-π-methane rearrangement in 4-(phenylmethyl)-2(5H)-furanones (1b-d) was investigated. Significant enhancement of efficiency in the reaction leading in high combined yields to two isomeric products (endo-2 and exo-2) was descussed in terms of both the substituent effects at the allyic methane carbon and the restrained feature of the ring-enrolled π-system.