INTRAMOLECULAR CARBENE ADDITION TO A TRIPLE BOND - MATRIX PHOTOCHEMISTRY OF ALPHA-DIAZO-2-ETHYNYLACETOPHENONE

Authors
KOMNICK P SANDER W
Citation
P. Komnick et W. Sander, INTRAMOLECULAR CARBENE ADDITION TO A TRIPLE BOND - MATRIX PHOTOCHEMISTRY OF ALPHA-DIAZO-2-ETHYNYLACETOPHENONE, Liebigs Annalen, (1), 1996, pp. 7-9
Citations number
13
Categorie Soggetti
Chemistry
Journal title
Liebigs Annalen → ACNP
ISSN journal
09473440
Issue
1
Year of publication
1996
Pages
7 - 9
Database
ISI
SICI code
0947-3440(1996):1<7:ICATAT>2.0.ZU;2-A
Abstract
The irradiation (lambda = 403 nm) of alpha-diazo-2-ethynylacetophenone (1a) in solid argon at 10 K leads to (2-ethynylphenyl)ketene (11) as the major product. A minor product is benzo-4-oxo-2,5-cyclohexadienyli dene (6) which on 475-nm irradiation reversibly rearranges to cyclopro p[a]inden-6(6aH)-one (5a). This demonstrates that the intramolecular a ddition of the carbene center to the double bond can compete with the Wolff rearrangement.