Overcrowded molecules. Part XI. A doubly ‘forbidden’ symmetry-allowed pericyclic reaction: the thermal rearrangement of (E)-2-benzylidene-(Z)-1-mesityl(phenyl)methyleneindane into (Z)-2-benzyl-1-mesityl(phenyl)methyleneindene

Autor:	Harry G. Heller, Howard Tucker, Keith Smith, John S. Hastings
Rok vydání:	1975
Předmět:	Antarafacial and suprafacial chemistry.chemical_compound Pericyclic reaction Hydrogen chemistry Stereochemistry Yield (chemistry) chemistry.chemical_element Molecule Conrotatory and disrotatory Fluorene Ring (chemistry) Medicinal chemistry
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :1545-1548
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19750001545
Popis:	(E)-2-Benzylidene-(Z)-1-mesityl(phenyl)methyleneindane cyclises by a disrotatory mode at 180 °C to give cis-9a,10-dihydro-5,10-diphenyl-6,8,9a-trimethyl-11H-benzo[b]fluorene, which, at this temperature, undergoes two ‘forbidden’ processes in concert, namely conrotatory ring opening and a suprafacial [1,7] hydrogen shift, to yield (Z)-2-benzyl-1-mesityl(phenyl)methyleneindene.
Databáze:	OpenAIRE
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