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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

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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.

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What this paper is about

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.

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Available 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 concepts: Chemistry, Succinic anhydride, Succinic acid, Succinates, Alkyl, Hydrolysis, Organic chemistry, Dicarboxylic acid

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