Reactions of mono- and bicyclic enol ethers with the I2-hydroperoxide system

被引：12

作者：

Terent'ev, Alexander O. ^{[1
]}

Zdvizhkov, Alexander T. ^{[1
]}

Kulakova, Alena N. ^{[1
]}

Novikov, Roman A. ^{[1
]}

Arzumanyan, Ashot V. ^{[1
]}

Nikishin, Gennady I. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

来源：

RSC ADVANCES | 2014年 / 4卷 / 15期

基金：

俄罗斯基础研究基金会;

关键词：

RING-OPENING POLYMERIZATION; AQUEOUS HYDROGEN-PEROXIDE; TERT-BUTYL HYDROPEROXIDE; ONE-POT SYNTHESIS; SP(3) C-H; ANTIMALARIAL ACTIVITY; GEM-DIHYDROPEROXIDES; METAL-FREE; ALKANE FUNCTIONALIZATION; CARBONYL-COMPOUNDS;

D O I：

10.1039/c3ra46462h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reactions of mono- and bicyclic enol ethers with I-2-H2O2, I-2-(BuOOH)-O-t, and I-2-tetrahydropyranyl hydroperoxide systems have been studied. It was shown that the reaction pathway depends on the nature of peroxide and the ring size. The reaction of 2,3-dihydrofuran and 3,4-dihydro-2H-pyran with the I-2-hydroperoxide system affords iodoperoxides, alpha-iodolactones, and alpha-iodohemiacetals. Bicyclic enol ethers are transformed into vicinal iodoperoxides only in the reaction with the I-2-H2O2 system, whereas the reaction with I-2-ButOOH gives the hydroperoxidation product.

引用

页码：7579 / 7587

页数：9

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