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.
Ballini R., Bosica G., Fiorini D., Righi P. (2002). Nitroalkanes and dimethyl maleate as source of 3-alkyl succinic anhydrides and (E)-3-alkylidene succinic anhydrides. SYNTHESIS, 2002(5), 681-685 [10.1055/s-2002-23548].
Nitroalkanes and dimethyl maleate as source of 3-alkyl succinic anhydrides and (E)-3-alkylidene succinic anhydrides
Righi P.
2002
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
