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

被引：30

作者：

Greer, A ^{[1
]}

Vassilikogiannakis, G ^{[1
]}

Lee, KC ^{[1
]}

Koffas, TS ^{[1
]}

Nahm, K ^{[1
]}

Foote, CS ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 21期

关键词：

D O I：

10.1021/jo991576d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the effects of added acid in the reaction of singlet oxygen with trans-4-propenylanisole (1). We provide evidence that solvent acidity modifies the behavior of the transient intermediates. Relative to reactions in aprotic 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.

引用

页码：6876 / 6878

页数：3

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