Unexpected one-pot formation of a selenophene by the reaction of 2,3-dichloropropene with selenium in hydrazine hydrate-KOH: Spectroscopic monitoring and quantum-chemical study

被引：1

作者：

Nikonova, Valentina S. ^{[1
]}

Korchevin, Nikolay A. ^{[1
]}

V. Manuylov, Victor ^{[1
]}

Borodina, Tatiana N. ^{[1
]}

Smirnov, Vladimir I. ^{[1
]}

Sinegovskaya, Lydia M. ^{[1
]}

Shagun, Vladimir A. ^{[1
]}

Rozentsveig, Igor B. ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2022年 / 982卷

关键词：

Selenium; Hydrazine hydrate; KOH; Selenophene; X-ray; Spectroscopic monitoring; Quanto-chemical research; Diselenides; MOLECULAR-STRUCTURE; DISULFIDE;

D O I：

10.1016/j.jorganchem.2022.122495

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A one-pot reaction of 2,3-dichloroprop-1-ene with selenium in the system hydrazine hydrate-KOH affords 1,2-bis((5-methylselenophen-3-yl)methyl)diselane. The structure of compound diselane has been proved by XRD, IR, and NMR ( 1 H, 13 C, 77Se) techniques. The reaction of 2,3-dichloroprop-1-ene with K2Se at 50 degrees C has been monitored by IR and UV spectroscopy. The mechanism of diselane formation includes the migra-tion of a selenium atom along the propenyl chain, which most likely occurs through the generation of a seleniranium intermediate. Such a transformation has been studied using quantum-chemical calculations (DFT (B3LYP)). (c) 2022 Published by Elsevier B.V.

引用

页数：9

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