ACETONE SENSITIZED INTRAMOLECULAR ORTHO PHOTOCYCLIZATION OF SUBSTITUTED 4-PHENOXYBUT-1-ENES AND 5-PHENOXYPENT-1-ENES

Authors
WAGNER PJ SMART RP
Citation
Pj. Wagner et Rp. Smart, ACETONE SENSITIZED INTRAMOLECULAR ORTHO PHOTOCYCLIZATION OF SUBSTITUTED 4-PHENOXYBUT-1-ENES AND 5-PHENOXYPENT-1-ENES, Tetrahedron letters, 36(29), 1995, pp. 5135-5138
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
29
Year of publication
1995
Pages
5135 - 5138
Database
ISI
SICI code
0040-4039(1995)36:29<5135:ASIOPO>2.0.ZU;2-T
Abstract
Several ortho and para (3-butenoxy) and (4-pentenoxy)benzonitriles and benzoate esters undergo the same internal ortho [2+2] cycloadditions under both direct (254 nm in CH3CN) and triplet sensitized irradiation (313 nm in acetone). The size of the ether rings fused to the cyclooc tatriene and bicyclooctadiene photoproducts govern the regio- and ster eoselectivities of their ensuing electrocyclic reactions.