NEIGHBORING GROUP PARTICIPATION IN A REGIOSELECTIVE AND STEREOSELECTIVE CHLORINATION OF A BICYCLO[2.2.2]OCTANONE

Authors
ALMQVIST F FREJD T
Citation
F. Almqvist et T. Frejd, NEIGHBORING GROUP PARTICIPATION IN A REGIOSELECTIVE AND STEREOSELECTIVE CHLORINATION OF A BICYCLO[2.2.2]OCTANONE, Journal of organic chemistry, 61(20), 1996, pp. 6947-6951
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
20
Year of publication
1996
Pages
6947 - 6951
Database
ISI
SICI code
0022-3263(1996)61:20<6947:NGPIAR>2.0.ZU;2-U
Abstract
The zinc chloride-mediated acetylation of the optically active silyl e nol ether 2a gave the beta-diketone 3a (48%) together with the regio- and stereoselectively chlorinated compound 4 (27%). The yield of 4 inc reased to 70% by starting from the O-acetyl derivative 2c. The chlorin ation most likely occurs via neighboring group participation by the en do acetoxy group.