✦ LIBER ✦
Intramolecular Carbene Addition to a Triple Bond - Matrix Photochemistry of α-Diazo-2-ethynylacetophenone
✍ Scribed by Komnick, Peter ;Sander, Wolfram
- Publisher
- John Wiley and Sons
- Year
- 2006
- Tongue
- English
- Weight
- 280 KB
- Volume
- 1996
- Category
- Article
- ISSN
- 0947-3440
No coin nor oath required. For personal study only.
✦ Synopsis
The irradiation (h = 403 nm) of a-diazo-2-ethynylacetophenone (1 a) in solid argon at 10 K leads to (2-ethynylpheny1)ketene (11) as the major product. A minor product is benzo-4oxo-2,5-cyclohexadienylidene (6) which on 475-nm irradi-ation reversibly rearranges to cycloprop[a]inden-6(6aH)-one (5a). This demonstrates that the intramolecular addition of the carbene center to the double bond can compete with the Wolff rearrangement.