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Stereochemistry of Norbornyl → Norpinyl Rearrangements
Author(s) -
Kirmse Wolfgang,
Minkner Dirk
Publication year - 1993
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199303851
Subject(s) - 2 norbornyl cation , carbocation , cationic polymerization , chemistry , stereochemistry , resonance (particle physics) , medicinal chemistry , physics , organic chemistry , particle physics
Bridged, chiral (A) and open, achiral intermediates (B) can occur during the cationic norbornyl → norpinyl rearrangement. As stereochemical results show, CN and CF 3 substituents favor A , double bonds (allyl resonance) in contrast favor B . Combination of these structural elements allows the proof of both types of carbocations.