%A X Fu
%A RA Moss
%A RR Sauers
%A P Wipf
%J Tetrahedron Letters
%T The fragmentation of exo-5-norbornenyl-2-oxychlorocarbene: Stereochemistry and mechanism
%X 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.
%N 24
%P 4265 - 4268
%V 46
%D 2005
%R 10.1016/j.tetlet.2005.03.208
%L pittir22246