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Computational study of the stereochemistry of intramolecular carbolithiation of an alkene by a secondary alkyllithium: stereochemistry change caused by a single THF molecule of solvation.

Liu, Hanbin and Deng, Kai and Cohen, Theodore and Jordan, Kenneth D (2007) Computational study of the stereochemistry of intramolecular carbolithiation of an alkene by a secondary alkyllithium: stereochemistry change caused by a single THF molecule of solvation. Org Lett, 9 (10). 1911 - 1914. ISSN 1523-7060

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Abstract

Theoretical calculations reveal that the 40:1 ratio of trans- to cis-2-methylcyclopentylmethyllithium formed in the cyclization of 6-lithio-1-heptene by intramolecular carbolithiation is due to steric crowding in the transition state for the cis-cyclization pathway when a single THF molecule complexes the lithium cation. In the absence of this specific solvation, the cis-cyclization pathway is predicted to be slightly favored.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Liu, Hanbin
Deng, Kai
Cohen, Theodore
Jordan, Kenneth Djordan@pitt.eduJORDAN
Date: 10 May 2007
Date Type: Publication
Journal or Publication Title: Org Lett
Volume: 9
Number: 10
Page Range: 1911 - 1914
DOI or Unique Handle: 10.1021/ol070453+
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
PubMed ID: 17439226
Date Deposited: 29 Oct 2012 21:21
Last Modified: 13 Oct 2017 23:01
URI: http://d-scholarship.pitt.edu/id/eprint/16080

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