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Azo Cope Rearrangements of Nonstabilized Azo Compounds
Author(s) -
Beck Karin,
Burghard Harald,
Fischer Gabriele,
Hünig Siegfried,
Reinold Petra
Publication year - 1987
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.198706721
Subject(s) - chemistry , cycloaddition , cope rearrangement , catalysis , computational chemistry , medicinal chemistry , stereochemistry , organic chemistry
The acid‐catalyzed [4 + 2] cycloaddition of the cyclic azines 1 with the 1,3‐dienes 2 leads to a mixture of the azo compounds 3 and the hydrazones 4.3 and 4 are interconverted by acid‐catalyzed [3.3] rearrangement. The structural dependence of this novel Cope rearrangement corresponds to the energy differences of 3 and 4 , which were estimated by force field calculations.X