Tetrahedron Letters p. 7143 - 7146 (1996)
Update date:2022-08-05
Topics:
Arrastia, Iosune
Cossio, Fernando P.
Reaction at room temperature between acyl chlorides and aromatic or α,β-unsaturated aldehydes in the presence of a tertiary base and in 5M lithium perchlorate-diethyl ether (5M LPDE) as solvent yields substituted alkenes in satisfactory yields. The reaction is formally conceived as a [2 + 2] cycloaddition between the aldehyde and the in situ formed ketene, followed by thermal decarboxylation of the intermediate 2 oxetanone. Ketene itself yields α,β-unsaturated acids under these reaction conditions.
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