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Reaction of Bicyclo[3.2.1]octenols with Thionyl Chloride. Preliminary paper
Author(s) -
Jefford C. W.,
Gunsher J. A.
Publication year - 1971
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.19710540531
Subject(s) - chemistry , thionyl chloride , allylic rearrangement , pentane , bicyclic molecule , ether , chloride , medicinal chemistry , organic chemistry , catalysis
The allylic 1‐methyl‐3‐bromobicyclo[3.2.1]octenyl exo ‐2 and exo ‐4 alcohols were treated with thionyl chloride in ether or pentane solution at 0°. In each case, a 50/50 mixture of exo allylic chlorides was obtained. No evidence for a predominant S N l ′ reaction was detected; reported cases of such S N l ′ processes using these conditions should therefore be treated with reserve.