Neighboring Group Participation in a Regio- and Stereoselective Chlorination of a Bicyclo[2.2.2]octanone
(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:
https://lup.lub.lu.se/record/31496
- author
- Almqvist, Fredrik and Frejd, Torbjörn LU
- organization
- publishing date
- 1996
- 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
- 2022-01-26 19:09:06
@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 (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}}, }