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Substituent effects on suspected phenonium ion reactions

✍ Scribed by Charles A. Kingsbury; D.C. Best

Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
189 KB
Volume
8
Category
Article
ISSN
0040-4039

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✦ Synopsis

We wish to report an nmr study of the alcohol-halide conversion in the 1,2-diphenyl-1-propyl system, with regard to the effect of substituents on the stereochemistry of the reaction. This study has bearing on the controversy concerning the phenonium ion, Cram' has recently presented the case for the phenonium ion in which stereochemical grounds played a prominent role in deciding the mechanism. Brown2 and co-workers have criticized this work on the basis of kinetic studies and prefer a conformational argument to explain the retention of configuration observed in the 3-phenyl-2-butyl system. Other studies3j7 have shown that a ,9-aryl group may shield one side of the open ion from attack of the nucleophile. Thus, configuration may be retained without participation.

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