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2,6‐Barbaralane Dicarbonitrile: A Probe for Dewar‐Hoffmann‐Type Homoaromatic Molecules
Author(s) -
Quast Helmut,
Görlach Yvonne,
Stawitz Josef
Publication year - 1981
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.198100931
Subject(s) - nonane , degenerate energy levels , chemistry , type (biology) , scale (ratio) , order (exchange) , bicyclic molecule , molecule , stereochemistry , physics , organic chemistry , geology , quantum mechanics , paleontology , finance , economics
In order to investigate the degenerate Cope rearrangement in substituted tricyclenes , compounds (1) and (2) were synthesized from bicyclo[3.3.1]nonane‐2,6‐dione. Even at −60 °C, (1) underwent the Cope rearrangement at a rate which was fast on the 13 C‐NMR time scale; in comparison. (2) serves as a model, static (non‐fluxional) system.