Journal of Organic Chemistry p. 4204 - 4208 (1981)
Update date:2022-09-26
Topics:
Kakiuchi, Kiyomi
Tsugaru, Toshinori
Tobe, Yoshito
Odaira, Yoshinobu
The acid-catalyzed rearrangement of <5.3.2>- and <5.4.2>propella-ε-lactones 9 and 10 in boiling acetic acid takes place readily to afford the 1,2-disubstituted cyclopentene 21 and cyclohexene 26 as the major products, respectively, while such lactone ring cleavage of the <4.3.2>- and <4.4.2>propella-δ-lactones 1 and 2 does not occur at all under similar conditions.The remarcable distinction in reactivity in the acid-catalyzed rearrangement between the ε-lactones and the δ-lactones is attributed to the effect of lactone ring size.
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Doi:10.1246/cl.1980.483
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