Regio- and Stereoselective Synthesis of a Novel Family of Unsaturated Compounds with the S-Se Bond and Their Cyclization to 2,3-Dihydro-1,4-thiaselenines

被引：14

作者：

Amosova, Svetlana V. ^{[1
]}

Filippov, Andrey S. ^{[1
]}

Potapov, Vladimir A. ^{[1
]}

Penzik, Maxim V. ^{[1
]}

Makhaeva, Nataliya A. ^{[1
]}

Amosova, Svetlana V. ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 08期

关键词：

2-bromomethyl-1; 3-thiaselenole; unsaturated selanyl sulfides; seleniranium intermediates; 1; 4-thiaselenines; thiols; UNEXPECTED REACTION; SE-77; NMR; ORGANOTELLURIUM COMPOUNDS; SELENIUM; 2-BROMOMETHYL-1,3-THIASELENOLE; ORGANOSELENIUM; REARRANGEMENT; MIMICS; DERIVATIVES; TELLURIUM;

D O I：

10.1055/s-0037-1610683

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regio-and stereoselective ring-opening reaction of 2-bromomethyl- 1,3-thiaselenole with thiols proceeded as nucleophilic attack at the selenium atom of seleniranium intermediate affording unsaturated selanyl sulfides, (Z)-CH2= CHSCH= CHSeSR, in up to 93% yield. Dithiols were involved in this reaction giving symmetrical polyunsaturated compounds with two S-Se bonds in 70-75% yields. Efficient synthesis of 2( organylsulfanyl)-2,3-dihydro-1,4-thiaselenines in 69-96% yields was developed by the acid-catalyzed cyclization of the unsaturated selanyl sulfides. Mild reaction conditions (room temperature) and short reaction times are important features of this methodology.

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页码：1832 / 1840

页数：9

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