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 29 条

[1] [Anonymous], 2010, CRC Handbook of Chemistry and Physics, V91
[2] "Green Is the Color": An Update on Ecofriendly Aspects of Organoselenium Chemistry
Azeredo, Juliano B.
Penteado, Filipe
Nascimento, Vanessa
Sancineto, Luca
Braga, Antonio L.
Lenardao, Eder Joao
Santi, Claudio
[J]. MOLECULES, 2022, 27 (05):
[3] ATOMIC CHARGES DERIVED FROM SEMIEMPIRICAL METHODS
BESLER, BH
MERZ, KM
KOLLMAN, PA
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) : 431 - 439
[4] DETERMINING ATOM-CENTERED MONOPOLES FROM MOLECULAR ELECTROSTATIC POTENTIALS - THE NEED FOR HIGH SAMPLING DENSITY IN FORMAMIDE CONFORMATIONAL-ANALYSIS
BRENEMAN, CM
WIBERG, KB
[J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (03) : 361 - 373
[5] ACETOXYSELENENYLATION OF OLEFINS FOR THE PREPARATION OF VINYLIC AND ALLYLIC ACETATES
ENGMAN, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) : 884 - 890
[6] Frisch M. J., 2019, GAUSSIAN 16
[7] Recent advances in the chemistry of selenophenoquinoline heterocycles: Synthesis, reactivity and biological activity
Gouda, Moustafa A.
Alansari, Rayan M.
Salem, Mohamed A.
Aljuhani, Ateyatallah
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2023, 1001
[8] Synthesis, Anti-Inflammatory, and Analgesic Evaluation of Some 2-Amino-5-Selenothiazoles
Gouda, Moustafa A.
Sherif, Yousery El-Sayed
Elsherbini, Mohamed S.
[J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2014, 189 (11) : 1633 - 1643
[9] Jain VimalK., 2017, ORGANOSELENIUM COMPO, DOI DOI 10.1039/9781788011907-00001
[10] Iodine-Mediated Alkoxyselenylation of Alkenes and Dienes with Elemental Selenium
Kurkutov, Evgeny O.
Shainyan, Bagrat A.
[J]. MOLECULES, 2022, 27 (19):

← 1 2 3 →