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Spiroconjugation
Author(s) -
Dürr Heinz,
Gleiter Rolf
Publication year - 1978
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.197805591
Subject(s) - carbanion , ion , chemistry , cycloaddition , computational chemistry , spectral line , perpendicular , stereochemistry , crystallography , organic chemistry , physics , catalysis , quantum mechanics , geometry , mathematics
Spiro compounds having mutually perpendicular π‐electron systems (“spiro‐polyenes”) exhibit a new kind of homoconjugation, which is designated as spiroconjugation. Spiro‐polyenes are readily accessible, e.g. by cycloaddition, by elimination of dinitrogen from 1,2‐diazaspiro‐polyenes, and by cyclization of carbenium ions or carbanions. The magnitude of the effect exerted by spiroconjugation is estimated by model calculations. It can be detected, for instance, by comparison of the electronic and photoelectron spectra of spiro‐polyenes and analogous compounds which are unable to undergo such interaction.