N. Toshima, I. Moritani
Jun 1, 1967
Citations
0
Influential Citations
3
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
When tetraphenylcyclopentadienone in 2-propanol was irradiated with ultraviolet light under a slow steam of nitrogen, 2, 3-diphenyl-1H-cyclopenta[l]phenanthrene and 1-oxo-2, 3-diphenyl-2, 3-dihydro-1H-cyclopenta[l]phenanthrene were obtained in 10% and 45% yields respectively. That is, a cis-stilbene skeleton cyclized oxidatively to a phenanthrene, while the carbonyl group was reduced to methylene, or olefin, to paraffin. In this reaction, a protic solvent was observed to be favorable. In contrast to this, tetraphenylcyclopentadiene gave no similar cyclized products under the same conditions. The mechanism of this photoreaction is proposed.