Effect of aza-substitution on the geometry and electrocyclization of pentadienyl anions: an apparent exception to the Woodward-Hoffmann rules?

Autor:	D. H. Hunter, R. P. Steiner, S. K. Sim
Rok vydání:	1977
Předmět:	Stereochemistry Chemistry Woodward–Hoffmann rules Computational chemistry Organic Chemistry Substitution (logic) General Chemistry Catalysis Cis–trans isomerism
Zdroj:	Canadian Journal of Chemistry. 55:1229-1241
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v77-171
Popis:	Two geometrical isomers of 1,3,5-triphenyl-1,3-pentadiene 1 have been prepared and characterized; trans,cis-1 and trans,trans-1.These have been used to prepare and characterize the 1,3,5-triphenylpentadienyl anion by quenching the lithium salt in THF and by following hydrogen–deuterium exchange in methanol-O-d with potassium methoxide. Attempts to induce electrocyclization (130 °C in THF or 200 °C in KOtBu–HOtBu) have proven unsuccessful. A comparison of the behaviour of this anion with the 2-aza and 2,4-diaza analogues has helped in elucidating the mechanisms for their electrocyclization and the apparent exception to the Woodward-Hoffmann rules.
Databáze:	OpenAIRE
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