Synthesis and garbene decomposition of functionally-substituted diazoacetic esters 4. 2-aminoethyl diazoacetates and N-(2-hydroxyethyl)-N-alkyldiazoacetamides

Abstract

1. Thermocatalytic decomposition of 2-(dialkylamino)ethyl diazoacetates with 2 mole % of an equimolar mixture of Cu and CuSO4 at 110°C, or with 2 mole % of Rh(OAc)2 at 60–100°C, is of the carbene type, and in the presence of dienes and acetylenes affords respectively the cyclopropane- and cyclopropenecarboxylate esters. 2. Facile intramolecular cyclization has been observed in N-(2-hydroxyethyl)-N-alkyl-diazoacetamides to give N-alkylmorpholin-3-ones on treatment with Cu and CuSO4, at 80–110°C.