PREPARATION OF 6-CHLORO-ALPHA-ALLENYLKETONES BY ACYLATION OF 3-BUTEN-1-YNES

Authors
SANTELLIROUVIER C LEFRERE S MAMAI M SANTELLI M
Citation
C. Santellirouvier et al., PREPARATION OF 6-CHLORO-ALPHA-ALLENYLKETONES BY ACYLATION OF 3-BUTEN-1-YNES, Tetrahedron letters, 36(14), 1995, pp. 2459-2460
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
14
Year of publication
1995
Pages
2459 - 2460
Database
ISI
SICI code
0040-4039(1995)36:14<2459:PO6BAO>2.0.ZU;2-U
Abstract
AlCl3 mediated acylation of 3-buten-1-yne derivatives with acyl chlori des yields a mixture of 5-chloro-2,3-pentadienones and 3-chloro-2,4-pe ntadienones. The proportion of allenylketones vs conjugated dienic ket ones depends on the substitution pattern of the starting enyne. Acylat ion of 5-acetoxy-3-buten-1-ynes leads to the corresponding allenylketo nes (6-acetoxy-5-chloro-2,3-pentadienones).