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Destabilized 2‐Norbornyl Cations
Author(s) -
Kirmse Wolfgang,
Mrotzeck Uwe,
Siegfried Rainer
Publication year - 1985
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.198500551
Subject(s) - 2 norbornyl cation , chemistry , substitution (logic) , stereochemistry , acceptor , physics , philosophy , quantum mechanics , linguistics
Four acceptor substituents at C‐5 and C‐6 destabilize the non‐classical structure of the 2‐norbornyl cation. The Wagner‐Meerwein rearrangement of 1 to 2 is completely forestalled by such a substitution pattern; however, 1 undergoes an exo, exo ‐3,2‐H shift to give 3 .