PREPARATION OF 2-VINYLCYCLOBUTANONES AND THEIR CONVERSION TO CYCLOPENTENONES

DOI: 10.1016/S0040-4039(00)94015-2

Source and publish data:

Tetrahedron Letters p. 4817 - 4820 (1983)

Update date:2022-08-16

Topics:

Authors:

Jackson, David A.

Rey, Max

Dreiding, Andre S.

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Article abstract of DOI:10.1016/S0040-4039(00)94015-2

Methyl- and ethyl-vinylketene 3 were added to several simple olefins 1 to afford alkylated 2-vinylcyclobutanones 4, which in turn rearranged to cyclopentenones 6 (via dienones 5A,B) or 7 (via 1,2-acyl migration) under acid catalysis.Evidence is presented for a cyclopropyl-carbinyl intermediate 8.

Full text of DOI:10.1016/S0040-4039(00)94015-2

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