Intramolecular photocycloaddition of 1,3-dienes with 2-pyridones

Authors
Sieburth, SM Zhang, FN
Citation
Sm. Sieburth et Fn. Zhang, Intramolecular photocycloaddition of 1,3-dienes with 2-pyridones, TETRAHEDR L, 40(18), 1999, pp. 3527-3530
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
18
Year of publication
1999
Pages
3527 - 3530
Database
ISI
SICI code
0040-4039(19990430)40:18<3527:IPO1W2>2.0.ZU;2-O
Abstract
Intramolecular photocycloaddition of a 2-pyridone and an acyclic 1,3-diene leads to formation of an apparent [2 + 2] product. This is presumably forme d by an initial [4 + 4] cycloaddition followed by Cope rearrangement of the highly strained product. The isolated 1,2-divinylcyclobutane undergoes a C ope rearrangement at 120 degrees C to give a polycyclic cyclooctadiene. (C) 1999 Elsevier Science Ltd. All rights reserved.