Symmetry-enforced conformational control of photochemical reactivity in 2-vinyl-1,3-terphenyl

Frederick D. Lewis, Xiaobing Zuo, Vladimir Gevorgyan, Michael Rubin

Research output: Contribution to journalArticle

30 Scopus citations

Abstract

The photocyclization of o-vinylbiphenyl to 9,10-dihydrophenanthrene occurs with very low quantum yield because of the low ground-state population of the reactive syn rotamer. 2-Vinyl-1,3-terphenyl exists as a single rotamer which undergoes highly efficient photocyclization. Irradiation at 77 K in a rigid glass permits observation of the 8a,9-dihydrophenanthrene which rearranges to the 9,10-dihydrophenanthrene upon warming of the glass. The barriers for photocyclization and the thermal sigmatropic hydrogen shift are both remarkably small.

Original languageEnglish (US)
Pages (from-to)13664-13665
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number46
DOIs
StatePublished - Nov 20 2002

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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