OMEGA-HYDROXY-ORTHO-QUINODIMETHANE - TRAPPING WITH TRIFLUOROACETONE AND PHOTOCYCLIZATION

Authors
GRIESBECK AG STADTMULLER S
Citation
Ag. Griesbeck et S. Stadtmuller, OMEGA-HYDROXY-ORTHO-QUINODIMETHANE - TRAPPING WITH TRIFLUOROACETONE AND PHOTOCYCLIZATION, Chemische Berichte, 126(9), 1993, pp. 2149-2150
Citations number
21
Categorie Soggetti
Chemistry
Journal title
Chemische Berichte → ACNP
ISSN journal
00092940
Volume
126
Issue
9
Year of publication
1993
Pages
2149 - 2150
Database
ISI
SICI code
0009-2940(1993)126:9<2149:O-TWTA>2.0.ZU;2-B
Abstract
Omega-Hydroxy-ortho-quinodimethane (2), generated by photoenolization of 2-methylbenzaldehyde (1) in benzene, is quantitatively trapped with trifluoroacetone to give the bicyclic hemiacetal 6 and the hydroxy al dehyde 7. A less effective trapping reaction is observed with benzalde hyde with the formation of the bicyclic hemiacetal 5. The formation of benzocyclobutenol 4 is probable due to a two-photon process involving electronically excited 2.