EFFECT OF PLACEMENT OF PHOSPHORUS IN A RING ON THE TRIPLET-SENSITIZEDPHOTOREARRANGEMENTS OF 2-PHENYLALLYL PHOSPHITES

Authors
GANAPATHY S CAMBRON RT DOCKERY KP WU YW HARRIS JM BENTRUDE WG
Citation
S. Ganapathy et al., EFFECT OF PLACEMENT OF PHOSPHORUS IN A RING ON THE TRIPLET-SENSITIZEDPHOTOREARRANGEMENTS OF 2-PHENYLALLYL PHOSPHITES, Tetrahedron letters, 34(38), 1993, pp. 5987-5990
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
38
Year of publication
1993
Pages
5987 - 5990
Database
ISI
SICI code
0040-4039(1993)34:38<5987:EOPOPI>2.0.ZU;2-X
Abstract
The triplet-sensitized photorearrangement of 2-phenylayllyl phosphite 4 is of the order 50-100 times less efficient than that for its acycli c counterpart, 1. This surprising effect can be understood in terms of the influence of the spiro ring system of 10 on the rate of its conve rsion to thermodynamically more stable 11 from which phosphonate 12 is formed.