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Sigmatropic Rearrangements Accompanying the Addition of Dichlorocarbene to Norbornadiene
Author(s) -
Jefford Charles W.,
Bernardinelli Gérald,
Rossier JeanClaude,
Zuber Jacques A.
Publication year - 1982
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.19820650520
Subject(s) - dichlorocarbene , norbornadiene , chemistry , sigmatropic reaction , adduct , bicyclic molecule , stereochemistry , photochemistry , medicinal chemistry , organic chemistry , catalysis
A new product arising from the reaction of dichlorocarbene with norbornadiene, 6 endo ‐(2,2‐dichlorovinyl)‐ cis ‐bicyclo[3.1.0]hex‐2‐ene, is described. It does not arise from the normal exo ‐l,2‐adduct, but possibly originates by sigmatropic rearrangement of an initially formed zwitterionic intermediate.