1 H NMR‐based kinetic and mechanistic study of unusual skeletal rearrangements of a spirobornyl tosylate derivative | Zendy

Lobb Kevin A. | Zendy; Kaye Perry T. | Zendy

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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.

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