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Nucleophilic Reactions at Tertiary Carbon. Part 3. σ‐ and π‐routes to the 9‐decalyl cation
Author(s) -
Becker Konrad B.,
Boschung André F.,
Geisel Manfred,
Grob Cyril A.
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560810
Subject(s) - chemistry , solvolysis , isomerization , nucleophile , medicinal chemistry , chloride , ion , product (mathematics) , hydrolysis , organic chemistry , catalysis , geometry , mathematics
The generation of the 9‐decalyl cation by solvolysis of cis ‐ and trans ‐9‐decalyl chloride ( 1 ) has been reinvestigated. The results of product, rate and isomerization studies implicate stereoisomeric ion pairs as intermediates, as in the case of the solvolysis of other stereoisomeric tertiary chlorides (Parts 1 and 2). On the other hand, both symmetrically and unsymmetrically solvated 9‐decalyl cations are indicated in the cyclization of 4‐(cyclohexen‐1‐yl)butyl tosylate. No evidence was obtained that conformational isomers of the 9‐decalyl cation play a role as product determining intermediates.