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Migration du groupe éthoxycarbonyle dans la transposition de Wagner‐Meerwein
Author(s) -
Phan Trung Hieu,
Dahn Hans
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.19760590137
Subject(s) - chemistry , olefin fiber , carbenium ion , dehydration , medicinal chemistry , leaving group , stereochemistry , catalysis , organic chemistry , biochemistry
Ethoxycarbonyl group migration in the Wagner‐Meerwein rearrangement . 13 β‐Hydroxy‐esters have been treated with P 2 O 5 in benzene at 80°. Olefin‐forming dehydration, when possible, was found to be the main reaction. When this is excluded, tertiary or benzylic hydroxy‐esters react in a manner most easily explained by migration of the COOEt group, thus avoiding the formation of α‐carbonyl‐carbenium ions. On the other hand, in primary hydroxy‐esters (incapable of direct olefin formation), phenyl and methyl groups migrate in preference to COOEt, indicating in this case a concerted reaction.