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Thermal Rearrangements
Author(s) -
von E. Doering W.,
Roth W. R.
Publication year - 1963
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.196301151
Subject(s) - cyclopropane , cope rearrangement , bond cleavage , double bond , cleavage (geology) , chemistry , ring (chemistry) , degenerate energy levels , stereochemistry , bicyclic molecule , crystallography , materials science , physics , polymer chemistry , organic chemistry , catalysis , quantum mechanics , fracture (geology) , composite material
The effect of conjugation with double bonds and (in cyclopropane) the effect of ring strain on the cleavage of carbon‐carbon bonds during thermal rearrangements is discussed. In particular, the Cope rearrangement and the geometry of its transition state are described. The structurally degenerate Cope rearrangement of bicyclo[5. 1. 0]octa‐2,5‐diene is discussed, and this compound is used to illustrate the concept of “fluctional structure”, which finds its extreme expression in the hypothetical compound, tricyclo[3. 3. 2. 0 4,6 ]‐deca‐2,7,9‐triene.