40628-44-2Relevant academic research and scientific papers
Synthesis and chemical transformations of 2-cyclopropyl-2-diazoacetates
Prokopenko,Okonnishnikova,Klimenko,Shulishov,Tomilov
, p. 1515 - 1521 (2007)
Methyl 2-cyclopropyl-2-diazoacetate was synthesized from acetylcyclopropane in few chemical steps in ～55% total yield. Its copper or rhodium-catalyzed dediazoniation exclusively proceeds through the intramolecular isomerization of generated cyclopropyl(methoxycarbonyl)carbene to 1-methoxycarbonylcyclobutene, irrespective of the presence or the absence of unsaturated compounds. However, in the presence of acrylates or strained cycloalkenes, this diazo ester is being slowly involved into the 1,3-dipolar cycloaddition, giving cyclopropyl- substituted pyrazolinecarboxylates, which in case of 1-pyrazolines easily lose nitrogen molecule to selectively afford 1-cyclopropylcyclopropanecarboxylate derivatives.
