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Synthesis 2019; 51(08): 1832-1840
DOI: 10.1055/s-0037-1610683
DOI: 10.1055/s-0037-1610683
paper
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
Further Information
Publication History
Received: 26 September 2018
Accepted after revision: 20 November 2018
Publication Date:
24 January 2019 (online)
Abstract
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.
Key words
2-bromomethyl-1,3-thiaselenole - unsaturated selanyl sulfides - seleniranium intermediates - 1,4-thiaselenines - thiolsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610683.
- Supporting Information
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