Advanced

Neighboring Group Participation in a Regio- and Stereoselective Chlorination of a Bicyclo[2.2.2]octanone

Almqvist, Fredrik and Frejd, Torbjörn LU (1996) In Journal of Organic Chemistry 61(20). p.6947-6951
Abstract
The zinc chloride-mediated acetylation of the optically active silyl enol ether 2a gave the beta-diketone 3a (48%) together with the regio- and stereoselectively chlorinated compound 4 (27%). The yield of 4 increased to 70% by starting from the O-acetyl derivative 2c. The chlorination most likely occurs via neighboring group participation by the endo acetoxy group.
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Organic Chemistry
volume
61
issue
20
pages
6947 - 6951
publisher
The American Chemical Society
external identifiers
  • scopus:0029802670
ISSN
1520-6904
DOI
10.1021/jo9607370
language
English
LU publication?
yes
id
427f41e6-3193-465a-9b65-18851e440ae0 (old id 31496)
date added to LUP
2007-06-19 14:27:20
date last changed
2017-01-01 04:36:06
@article{427f41e6-3193-465a-9b65-18851e440ae0,
  abstract     = {The zinc chloride-mediated acetylation of the optically active silyl enol ether 2a gave the beta-diketone 3a (48%) together with the regio- and stereoselectively chlorinated compound 4 (27%). The yield of 4 increased to 70% by starting from the O-acetyl derivative 2c. The chlorination most likely occurs via neighboring group participation by the endo acetoxy group.},
  author       = {Almqvist, Fredrik and Frejd, Torbjörn},
  issn         = {1520-6904},
  language     = {eng},
  number       = {20},
  pages        = {6947--6951},
  publisher    = {The American Chemical Society},
  series       = {Journal of Organic Chemistry},
  title        = {Neighboring Group Participation in a Regio- and Stereoselective Chlorination of a Bicyclo[2.2.2]octanone},
  url          = {http://dx.doi.org/10.1021/jo9607370},
  volume       = {61},
  year         = {1996},
}