SOLID-STATE PHOTODIMERIZATION OF 2-PHENYLETHENYL ENAMIDES

Authors
SONG FB SNOOK JH FOXMAN BM SNIDER BB
Citation
Fb. Song et al., SOLID-STATE PHOTODIMERIZATION OF 2-PHENYLETHENYL ENAMIDES, Tetrahedron, 54(43), 1998, pp. 13035-13044
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
43
Year of publication
1998
Pages
13035 - 13044
Database
ISI
SICI code
0040-4020(1998)54:43<13035:SPO2E>2.0.ZU;2-U
Abstract
Enamides 3a-c and 6 crystallize in alpha-packing modes with short inte rmolecular distances of 3.7-4.0 Angstrom between alkene carbon atoms o f adjacent molecules related by a center of symmetry. Irradiation at 3 50 nm of these crystalline tertiary phenylethenyl enamides affords hea d-to tail dimers 8a-c and 9, respectively, in 87-92% yield, in marked contrast to the E to Z isomerization that is the exclusive reaction up on solution irradiation of enamides 3a and 6. (C) 1998 Elsevier Scienc e Ltd. All rights reserved.