Photochemical Generation and Reversible Cycloaromatization of a Nine-Membered Ring Cyclic Enediyne

被引：47

作者：

Pandithavidana, Dinesh R. ^{[1
]}

Poloukhtine, Andrei ^{[1
]}

Popik, Vladimir V. ^{[1
]}

机构：

[1] Univ Georgia, Dept Chem, Athens, GA 30677 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 01期

基金：

美国国家科学基金会;

关键词：

ANTITUMOR ANTIBIOTIC DYNEMICIN; INDUCED BERGMAN CYCLIZATION; BENZYNE-TYPE BIRADICALS; METAL CHARGE-TRANSFER; DNA-CLEAVAGE; P-BENZYNE; HYDROGEN ABSTRACTION; CYCLOPROPENONE CHEMISTRY; TRIGGERING DEVICES; C-1027; CHROMOPHORE;

D O I：

10.1021/ja8077076

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Irradiation of the nine-membered ring enediyne precursor, which has one of its triple bonds masked as cyclopropenone, efficiently (Phi = 0.34) generates the reactive 4,5-benzocyclonona-2,6-diynol. The latter rapidly equilibrates with the corresponding 1,4-didehydronaphthalene diradical and then undergoes rate-limiting hydrogen abstraction to produce the ultimate product of the Bergman cyclization, benz[f]indanol.

引用

页码：351 / 356

页数：6

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