INTRAMOLECULAR PHOTOCYCLOADDITION OF CYCLOPROPENES - RING STRAIN-DRIVEN HYDROGEN-TRANSFER OF 1,4-BIRADICAL INTERMEDIATES

Authors
KOHMOTO S KOYANO I KISHIKAWA K YAMAMOTO M YAMADA K
Citation
S. Kohmoto et al., INTRAMOLECULAR PHOTOCYCLOADDITION OF CYCLOPROPENES - RING STRAIN-DRIVEN HYDROGEN-TRANSFER OF 1,4-BIRADICAL INTERMEDIATES, Tetrahedron letters, 37(49), 1996, pp. 8879-8882
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
49
Year of publication
1996
Pages
8879 - 8882
Database
ISI
SICI code
0040-4039(1996)37:49<8879:IPOC-R>2.0.ZU;2-2
Abstract
Intramolecular photocycloaddition of cyclopropene carboxylic acid ally lic esters 1 results in an exclusive formation of 5-oxaspiro[2.4]hepta -4-ones 2, the hydrogen transferred rearrangement products, with induc tion of three stereogenic centers. Ring strain is crucial to alter the course of reaction from the [2+2] photocycloaddtion to the hydrogen t ransfer. Copyright (C) 1996 Elsevier Science Ltd.