2,6‐Barbaralane Dicarbonitrile: A Probe for Dewar‐Hoffmann‐Type Homoaromatic Molecules | Zendy

Quast Helmut | Zendy; Görlach Yvonne | Zendy; Stawitz Josef | Zendy

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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.

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