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Overcrowded molecules. Part 11. 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

Hastings, John S., Heller, Harry G., Tucker, Howard and Smith, Keith 1975. Overcrowded molecules. Part 11. 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. Journal of the Chemical Society, Perkin Transactions 1 (16) , pp. 1545-1548. 10.1039/P19750001545

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Abstract

(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.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: RSC Publishing
ISSN: 0300-922X
Last Modified: 04 Jun 2017 02:50
URI: http://orca.cardiff.ac.uk/id/eprint/12587

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