Azirinium ylides from alkoxycarbonylcarbenoids and 2H-azirines: Generation and transformations

Pleiades Publishing Ltd - Tập 42 - Trang 515-526 - 2006
A. F. Khlebnikov1, M. S. Novikov1, A. A. Amer1, R. R. Kostikov1, J. Magull2, D. Vidovic2
1St. Petersburg State University, St. Petersburg, Russia
2Institut für anorganische Chemie, Georg-August-Universitat, Göttingen, Germany

Tóm tắt

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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