Acid-Catalyzed Rearrangement of [5.n.2]Propella-e-lactones

Kiyomi Kakiuchi*, Toshinori Tsugaru, Tobe Yoshito, Yoshinobu Odaira

*Corresponding author for this work

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

The acid-catalyzed rearrangement of [5.3.2]- and [5.4.2]propella-e-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 remarkable distinction in reactivity in the acid-catalyzed rearrangement between the e-lactones and the δ-lactones is attributed to the effect of lactone ring size.

Original languageEnglish
Pages (from-to)4204-4208
Number of pages5
JournalJournal of Organic Chemistry
Volume46
Issue number21
DOIs
StatePublished - 1 Jan 1981

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