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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