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The fragmentation of exo-5-norbornenyl-2-oxychlorocarbene: Stereochemistry and mechanism

Fu, X and Moss, RA and Sauers, RR and Wipf, P (2005) The fragmentation of exo-5-norbornenyl-2-oxychlorocarbene: Stereochemistry and mechanism. Tetrahedron Letters, 46 (24). 4265 - 4268. ISSN 0040-4039

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Abstract

The fragmentation of (S)-exo-5-norbornenyl-2-oxychlorocarbene (3) affords (S)-exo-5-norbornenyl-2-chloride (4), (R)-endo-5-norbornenyl-2-chloride (5), and (S)-3-nortricyclyl chloride (6) with varying degrees of enantiomeric excess. A weighted blend of SNi fragmentation and escape to norbornenyl/nortricyclyl ion pairs rationalizes the stereochemical results. © 2005 Elsevier Ltd. All rights reserved.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Fu, X
Moss, RA
Sauers, RR
Wipf, Ppwipf@pitt.eduPWIPF
Date: 13 June 2005
Date Type: Publication
Journal or Publication Title: Tetrahedron Letters
Volume: 46
Number: 24
Page Range: 4265 - 4268
DOI or Unique Handle: 10.1016/j.tetlet.2005.03.208
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4039
Date Deposited: 18 Jul 2014 21:05
Last Modified: 02 Feb 2019 15:57
URI: http://d-scholarship.pitt.edu/id/eprint/22246

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