Nitroalkanes and Dimethyl Maleate as Source of 3-Alkyl Succinic Anhydrides and (E)-3-Alkylidene Succinic Anhydrides

Roberto Ballini; Giovanna Bosica; Dennis Fiorini; Paolo Righi

doi:10.1055/s-2002-23548

PAPER

Nitroalkanes and Dimethyl Maleate as Source of 3-Alkyl Succinic Anhydrides and (E)-3-Alkylidene Succinic Anhydrides

Roberto Ballini*^a, Giovanna Bosica^a, Dennis Fiorini^a, Paolo Righi^b
^a Dipartimento di Scienze Chimiche dell’Università, Via S. Agostino 1, 62032 Camerino (MC), Italy
Fax: +39(0737)402297; e-Mail: roberto.ballini@unicam.it;
^b Dipartimento di Chimica Organica ”A. Mangini" dell’Università, V.le Risorgimento 4, 40136 Bologna, Italy

Abstract

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Abstract

Nitroalkanes react with dimethyl maleate giving a tandem Michael addition/elimination of nitrous acid. The obtained (E)-2-alkylidene dimethyl succinates are: (i) reduced to the corresponding 2-alkyl dimethyl succinates which after hydrolysis produce 1,4-dicarboxylic acids that are prone to convert into the corresponding 3-alkyl succinic anhydrides or (ii) hydrolysed to (E)-2-alkylidene-succinic acids that are easily cyclised to (E)-3-alkylidene succinic anhydrides.

Key words

nitroalkanes - 3-alkyl succinic anhydrides - 3-alkylidene succinic anhydrides - dimethyl maleate - heterocyclic compounds

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References

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