REINVESTIGATION IN THE PHOTOREACTION OF 1-NAPHTHALENECARBONITRILE ANDFURAN

Authors
NOH T KIM D
Citation
T. Noh et D. Kim, REINVESTIGATION IN THE PHOTOREACTION OF 1-NAPHTHALENECARBONITRILE ANDFURAN, Tetrahedron letters, 37(52), 1996, pp. 9329-9332
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
52
Year of publication
1996
Pages
9329 - 9332
Database
ISI
SICI code
0040-4039(1996)37:52<9329:RITPO1>2.0.ZU;2-N
Abstract
Photocycloaddition of furan to 1-naphthalenecarbonitrile (1) was reinv estigated. irradiation of the mixture through Pyrex filter yielded end o-[4+4] adduct (2) and syn-[2+2] adduct (4). Considering the secondary orbital interaction in the singlet-slate [4+4] photocycloaddition, th e favorable formation of exo-[4+4] cyclodimer (3) over 2 followed by a facile Cope rearrangement was proposed for the formation of 4, and co nfirmed by a low temperature irradiation experiment. Copyright (C) 199 6 Elsevier Science Ltd