Abstract
Thermal, photolytic, and thermocatalytic decomposition of methyl diazoacetate (MDA) in the presence of Rh2(OAc)4 or Cu(acac)2 in refluxing pyridine afforded isomeric trans,cis- and cis,trans-3,4,5,6-tetra(methoxycarbonyl)-1,4,5,6-tetrahydropyridazines (∼1 : 1) in a total yield of 30—70%. Decomposition of MDA in refluxing o-xylene in the presence of Rh2(OAc)4 and pyridine (20 mol.%) gave rise to 2,3,4,5-tetra(methoxycarbonyl)pyrrole in a yield of up to 40%. In these transformations of MDA, neither dimethyl fumarate (or dimethyl maleate) nor the corresponding 2-pyrazolines were generated as intermediates.
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