Spiroconjugation

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Abstract
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.

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