Abstract
Pyrolysis of ethyl maleate leads to cis→trans inversion, with concurrent alkyl–oxygen scission (A1; predominating), acyl–oxygen scission (B2), and decarboxylation (C2). For methyl maleate, A1 scission is structurally precluded; there is cis→trans inversion, with concurrent B2 and C2 scission. Ethylene diacrylate and dimethacrylate both undergo a predominating double C2 scission, in competition with A1 scission and a minor B2 scission: the products of the primary A1 scission partially interact to give an ethylidene diester, followed by disproportionation and further breakdown. All pyrolyses were at ca. 450–500° in the vapour phase. The bearing of these results on the pyrolysis of poly(ethylene fumarate) is discussed.
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