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 language | English (US) |
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Pages (from-to) | 13664-13665 |
Number of pages | 2 |
Journal | Journal of the American Chemical Society |
Volume | 124 |
Issue number | 46 |
DOIs | |
State | Published - Nov 20 2002 |
ASJC Scopus subject areas
- General Chemistry
- Biochemistry
- Catalysis
- Colloid and Surface Chemistry