Sulfate radical anions (SO4•-) as donor of atomic oxygen in anionic transannular, self-terminating, oxidative radical cyclizations

被引：37

作者：

Wille, U ^{[1
]}

机构：

[1] Univ Kiel, Inst Organ Chem, D-24098 Kiel, Germany

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 22期

关键词：

D O I：

10.1021/ol006527y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] SO4.- generated by the Fenton redox system S2O82--Fe2+ induces a novel anionic, transannular, self-terminating, oxidative radical cyclization in the reactions with the ten-membered cycloalkyne 1 and the cycloalkynone 7, yielding the bicyclic ketones 5 and 6 or the alpha,beta -epoxy ketones 8 and 9, respectively. In these reactions SO4.- acts as an oxygen transfer reagent and can thus be considered as a donor of atomic oxygen in solution.

引用

页码：3485 / 3488

页数：4

共 16 条

[1]

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[2]

Curran D. P., 1996, STEREOCHEMISTRY RADI

[3]

CURRAN DP, 1996, STEREOCHEMISTRY RADI, P26

[4] ELECTRON-SPIN RESONANCE STUDIES .68. ADDITION VERSUS OVERALL ONE-ELECTRON ABSTRACTION IN THE OXIDATION OF ALKENES AND DIENES BY SO4-., CL2-., AND .OH IN ACIDIC AQUEOUS-SOLUTION [J].