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Facteurs stériques influençant la transposition de Wagner‐Meerwein des carbocations de type pinanyle
Author(s) -
Barthélémy Michel,
Gianfermi Anne,
Bessière Yvonne
Publication year - 1976
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.19760590546
Subject(s) - chemistry , carbocation , protonation , isomerization , steric effects , cope rearrangement , stereochemistry , ion , medicinal chemistry , organic chemistry , catalysis
Steric factors influencing Wagner‐Meerwein rearrangement of pinanyl carboniumions. The course of the Wagner‐Meerwein rearrangement of ions obtained by protonation of substituted α‐ or β‐pinenes is strongly dependent on the configuration of the substituents. The situation is complicated by the possibility of double bond isomerisation (α‐→β‐pinenes) before rearrangement. Simple rules for predicting the products are given.