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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.
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author
and
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 (ACS)
external identifiers
  • scopus:0029802670
ISSN
1520-6904
DOI
10.1021/jo9607370
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
427f41e6-3193-465a-9b65-18851e440ae0 (old id 31496)
date added to LUP
2016-04-01 11:50:58
date last changed
2025-10-14 10:03:53
@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 (ACS)}},
  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}},
  doi          = {{10.1021/jo9607370}},
  volume       = {{61}},
  year         = {{1996}},
}