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1 H NMR‐based kinetic and mechanistic study of unusual skeletal rearrangements of a spirobornyl tosylate derivative
Author(s) -
Lobb Kevin A.,
Kaye Perry T.
Publication year - 2011
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1699
Subject(s) - chemistry , racemization , tandem , autocatalysis , derivative (finance) , computational chemistry , solvent , kinetics , proton nmr , stereochemistry , organic chemistry , catalysis , materials science , physics , quantum mechanics , financial economics , economics , composite material
1 H NMR analysis of the kinetics of skeletal rearrangement of optically pure 3,3‐xylyl‐2‐ exo ‐bornyl tosylate in CDCl 3 indicates the operation of tandem autocatalytic and pseudo‐first‐order transformations, leading sequentially to a pair of isomeric camphene derivatives and involving partial racemization. Changing the solvent system has been shown to permit the chemoselective isolation of either of the isomeric camphenes. Copyright © 2010 John Wiley & Sons, Ltd.