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Novel pathways of interaction of maleic anhydride derivatives with phosphorus(III) compounds: synthesis and characterisation of N,N,N′,N′ -tetraethyl-2,3-diphenylbut-2-enediamide and 3-dihydrofuranylidene-4-phosphorylidene–oxolane-2,5,5′-trione

Lenar I. Musin, Andrei V. Bogdanov, Dmitry B. Krivolapov, Alexey B. Dobrynin, Rashid Z. Musin, Viktor N. Khrustalev, and Vladimir F. Mironov

A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Centre, Russian Academy of Sciences, Arbuzov str. 8, 420088 Kazan, Russia

 

E-mail: abogdanov@inbox.ru

Abstract: Maleic anhydride undergoes C-phosphorylation under the action of tris(diethylamino)phosphine to afford 3-dihydrofuranylidene-4-phosphorylidene-oxolane-2,5,5′-trione whereas 2,3-diphenylmaleic anhydride under the same conditions turns into N,N,N′,N′-tetraethyl-2,3-diphenylbut-2-enediamide. The latter reaction can serve as a novel approach for the synthesis of dicarboxylic acids diamides from corresponding cyclic anhydrides. Their structures were established by NMR and X-ray diffraction.

Keywords: maleic anhydride – nucleophilic addition – amidation – ylides – crystal structure

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0094

 

Chemical Papers 69 (7) 1012–1015 (2015)

Wednesday, May 29, 2024

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