Synthesis of novel β-aryl-β-(methylthio)acroleins via Vilsmeier–Haack protocol as potential 1,3-dielectrophilic three-carbon building blocks

Byre Gowda, G. and Charanraj, T. P. and Pradeepa Kumara, C. S. and Ramesh, N. and Thomas, S. P. and Sadashiva, M. P. and Junjappa, H. (2014) Synthesis of novel β-aryl-β-(methylthio)acroleins via Vilsmeier–Haack protocol as potential 1,3-dielectrophilic three-carbon building blocks. Tetrahedron Letters, 55 (32). pp. 4475-4479. ISSN 0040-4039

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Abstract

A new general route for the synthesis of novel β-aryl-β- (methylthio)acroleins, a class of stable potential 1,3-dielectrophilic synthons, has been reported. The overall protocol involves treatment of either β-chloroacroleins or their precursor iminium salts (generated in situ from the corresponding active methylene ketones under Vilsmeier-Haack reaction conditions) with S,S-dimethyldithiocarbonates (DDC)/aqueous KOH in either a one-pot or two-step process. The dimethyldithiocarbonate (DDC)/30% aqueous KOH has been shown to be an excellent source of methylthiolate anion.

Item Type:	Article
Uncontrolled Keywords:	X ray diffraction, polymerization, stereochemistry, synthesis, article, room temperature, chlorinated hydrocarbon, acetic acid, catalyst, methyl group, electron, acid anhydride, carbon monoxide, acrolein derivative, carbonic acid derivative, electrophilicity, ketone derivative, nucleophilicity, potassium hydroxide, tetrabutylammonium, Vilsmeier Haack reaction
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	Arshiya Kousar Library Assistant
Date Deposited:	18 Jun 2019 05:05
Last Modified:	18 Jun 2019 05:05
URI:	http://eprints.uni-mysore.ac.in/id/eprint/3169

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