Reaction of singlet oxygen with trans-4-propenylanisole. Formation of [2+2] products with added acid

Authors
Greer, A Vassilikogiannakis, G Lee, KC Koffas, TS Nahm, K Foote, CS
Citation
A. Greer et al., Reaction of singlet oxygen with trans-4-propenylanisole. Formation of [2+2] products with added acid, J ORG CHEM, 65(21), 2000, pp. 6876-6878
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
21
Year of publication
2000
Pages
6876 - 6878
Database
ISI
SICI code
0022-3263(20001020)65:21<6876:ROSOWT>2.0.ZU;2-Q
Abstract
We report the effects of added acid in the reaction of singlet oxygen with trans-4-propenylanisole (1). We provide evidence that solvent acidity modif ies the behavior of the transient intermediates. Relative to reactions in a protic solvent, enhanced dioxetane concentrations are observed in MeOH and in nonprotic solvents with acid. We suggest a new mechanism that invokes a proton transfer from MeOH and benzoic acid to perepoxide (2) and zwitterion (3) intermediates.