Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives

Venkateswarlu, Cheerladinne and Chandrasekaran, Srinivasan (2015) Hydrochalcogenation of Symmetrical and Unsymmetrical Buta-1,3-diynes with Diaryl Dichalcogenides: Facile Entry to (Z)-1-(Organylchalcogeno)but-1-en-3-yne Derivatives. In: SYNTHESIS-STUTTGART, 47 (3). pp. 395-410.

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Abstract

This work describes an efficient and stereoselective method for the hydrothiolation and -selenation of buta-1,3-diyne derivatives using diaryl disulfides or diselenides, respectively. In the presence of rongalite (HOCH2SO2Na) and potassium carbonate, buta-1,3-diynes undergo stereoselective addition of the thiolate or selenide anion generated in situ from diaryl disulfides or diselenides to afford the corresponding (Z)-1-sulfanyl-or (Z)-1-selanylalk-1-en-3-yne derivatives, respectively. The reaction of buta-1,3-diynes with diaryl disulfides or diselenides at higher temperature (70 degrees C) gave a mixture of monothiolation/selenation and bisthiolation/selenation products in moderate to good yields.

Item Type:	Journal Article
Publication:	SYNTHESIS-STUTTGART
Publisher:	GEORG THIEME VERLAG KG
Additional Information:	Copy right for this article belongs to the GEORG THIEME VERLAG KG, RUDIGERSTR 14, D-70469 STUTTGART, GERMANY
Keywords:	hydrochalcogenation; buta-1,3-diynes; aryl dichalcogenides; rongalite; reductive cleavage
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	04 Mar 2015 12:07
Last Modified:	04 Mar 2015 12:07
URI:	http://eprints.iisc.ac.in/id/eprint/50949

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