Markovnikov vs anti-Markovnikov iodine-mediated acyloxyselenenylation of alkenes and dienes with elemental selenium and carboxylic acids

被引：1

作者：

Kurkutov, Evgeny O. ^{[1
]}

Gubal, Semen Yu. ^{[1
]}

Ivanova, Alexandra B. ^{[1
]}

V. Ushakova, Irina ^{[1
]}

Shainyan, Bagrat A. ^{[1
]}

机构：

[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, Irkutsk 664033, Russia

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2023年 / 1003卷

关键词：

Elemental selenium; Alkenes; Dienes; Iodine -mediated additon; Acyloxyselenenylation; ACETOXYSELENENYLATION; OLEFINS;

D O I：

10.1016/j.jorganchem.2023.122919

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The iodine-mediated one-pot synthesis of new bis(beta-acyloxyorganyl)selenides from elemental selenium, olefins and carboxylic acids has been developed. The reaction with terminal alkenes leads to the selenides of the Markovnikov type. In the presence of NaOH the regioselectivity of the reaction is changed in favor of the formation of the anti-Markovnikov adducts. With 1,4-cyclohexadiene, the reaction proceeds via addition to only one double bond to afford selenobis(cyclohex-4-ene-2,1-diyl) dibutyrate, whereas with 1,5-cyclooctadiene the bicyclic monoadduct, 9-selenabicyclo[3.3.1]nonane-2,6-diyl dibutyrate, is formed. The mechanism explaining the different regioselectivity is proposed and supported by theoretical calculations.

引用

页数：8

共 20 条

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