Novel photo-rearrangement of 1,5-di(p-methoxyphenyl)-6,7-dioxabicyclo[3.2.2]nonane through an O-neophyl-type 1,2-aryl shift: evidence for a 1,6-dioxyl diradical intermediate

Authors
Kamata, M Komatsu, K
Citation
M. Kamata et K. Komatsu, Novel photo-rearrangement of 1,5-di(p-methoxyphenyl)-6,7-dioxabicyclo[3.2.2]nonane through an O-neophyl-type 1,2-aryl shift: evidence for a 1,6-dioxyl diradical intermediate, TETRAHEDR L, 42(51), 2001, pp. 9027-9030
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
51
Year of publication
2001
Pages
9027 - 9030
Database
ISI
SICI code
0040-4039(200112)42:51<9027:NPO1>2.0.ZU;2-F
Abstract
Photolysis and thermolysis of 1,5-diaryl-6.7-dioxabicyclo[3.2.2]nonane 1a-c (a: Ar=p-MeOC6H4. b: Ar = p-MeC6H4, C: Ar=Ph) were investigated. (p-Methox yphenyl)-substituted 1a underwent a novel photo-initiated O-neophyl-type 1. 2-aryl shift to afford 1-(p-methoxyphenyl)oxy-5-(p-methoxyphenyl)-8-oxabicy clo[3.2.1]octane 7a along with a small amount of 1-(p-methoxyphenyl)-3-(2-( 4 ' -methoxyphenyl)tetrahydrofuran-2-yl)propan-1-one 4a through an 1.6-diox yl diradical intermediate, while the thermolysis mainly afforded the 1,5-di (p-methoxyphenyl)pentan-1,5-dione 5a and 1,4-di(p-methoxyphenyl)butan-1,4-d ione 8a. (C) 2001 Elsevier Science Ltd. All rights reserved.