Journal
TETRAHEDRON LETTERS
Volume 45, Issue 31, Pages 6003-6006Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.06.038
Keywords
azirines; strained azomethine ylides; alpha-diazo esters; carbenoids; 2-azabuta-1,4-dienes; pyrrolines
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Thermocatalytic decomposition of diazo esters in the presence of 3-aryl-2H-azirines gives rise to azirinium ylides. The latter preferentially transform via isomerization into 2-azabuta-13-diene derivatives or, with excess diazo compound, via reaction with the Rh-carbenoid to form 3,4-dihydro-2H-pyrrole derivatives. In contrast, ylides generated front 2-monosubstituted or 2,2-disubstituted 3-phenyl-2H-azirines transform exclusively via isomerization into the corresponding 2-azabuta-1,3-dienes in high yields. (C) 2004 Published by Elsevier Ltd.
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