Abstract
Dirhodium tetraacetate-catalyzed decomposition of diazo esters in the presence of 3-aryl-2H-azirines having no substituent in the 2-position gives rise to azirinium ylides which then undergo isomerization into 2-azabuta-1,3-diene derivatives or (in the presence of excess diazo ester) react with the corresponding rhodium carbenoid to form substituted 3,4-dihydro-2H-pyrroles. 2-Mono-and 2,2-disubstituted 3-phenyl-2H-azirines react with rhodium carbenoids generated from diazo esters to give azirinium ylides which are converted into the corresponding 2-azabuta-1,3-dienes.
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Original Russian Text © A.F. Khlebnikov, M.S. Novikov, A.A. Amer, R.R. Kostikov, J. Magull. D. Vidovic, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 4, pp. 533–544.
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Khlebnikov, A.F., Novikov, M.S., Amer, A.A. et al. Azirinium ylides from alkoxycarbonylcarbenoids and 2H-azirines: Generation and transformations. Russ J Org Chem 42, 515–526 (2006). https://doi.org/10.1134/S1070428006040075
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DOI: https://doi.org/10.1134/S1070428006040075