PREPARATION OF DELTA-CHLORO-ALPHA-ALLENYL KETONES BY ACYLATION OF 3-BUTEN-1-YNES

Authors
SANTELLIROUVIER C LEFRERE S SANTELLI M
Citation
C. Santellirouvier et al., PREPARATION OF DELTA-CHLORO-ALPHA-ALLENYL KETONES BY ACYLATION OF 3-BUTEN-1-YNES, Journal of organic chemistry, 61(19), 1996, pp. 6678-6684
Citations number
57
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
19
Year of publication
1996
Pages
6678 - 6684
Database
ISI
SICI code
0022-3263(1996)61:19<6678:PODKBA>2.0.ZU;2-R
Abstract
AlC(l)3-mediated acylation of 3-buten-1-yne derivatives with acyl chlo rides yields a mixture of 5-chloro-2,3-pentadienones and 3-chloro-2,4- pentadienones. The proportion of allenyl ketones vs conjugated dienic ketones depends on the substitution pattern of the starting enyne, Acy lation of 5-acetoxy-3-buten-1-ynes leads to the corresponding allenyl ketones (6-acetoxy-5-chloro-2,3-pentadienones).