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

• Published in: Chemical papers Vol. 69; no. 7; pp. 1012 - 1015
• Main Authors: Musin, Lenar I., Bogdanov, Andrei V., Krivolapov, Dmitry B., Dobrynin, Alexey B., Musin, Rashid Z., Khrustalev, Viktor N., Mironov, Vladimir F.
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01.07.2015; De Gruyter Open
• Subjects: amidation; Biochemistry; Biotechnology; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; crystal structure; Industrial Chemistry/Chemical Engineering; maleic anhydride; Materials Science; Medicinal Chemistry; nucleophilic addition; Short Communication; ylides; maleic anhydride; amidation; crystal structure; ylides; nucleophilic addition
• ISSN: 0366-6352; 1336-9075
• DOI: 10.1515/chempap-2015-0094

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.