ACCENTUATION OF THE DI-?-METHANE REACTIVITY BY CENTRAL CARBON SUBSTITUTION IN THE 4-(PHENYLMETHYL)-2(5H)-FURANONE SYSTEM

Article abstract of DOI:10.3987/COM-90-5502

The effect of 'central methane' substitution on the di-?-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 discussed in terms of both the substituent effects at the allylic methane carbon and the restrained feature of the ring-enrolled ?-system.