Journal
TETRAHEDRON LETTERS
Volume 53, Issue 43, Pages 5777-5780Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.08.063
Keywords
Azirines; Diazo compounds; Carbenoids; Ylides; 2-Azabuta-1,3-dienes; 2,3-Dihydroazetes; Electrocyclic reactions
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Funding
- Russian Foundation for Basic Research [11-03-00186]
- Federal Grant-in-Aid Program Human Capital for Science and Education in Innovative Russia [16.740.11.0442]
- Saint Petersburg State University [12.38.78.2012]
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The Rh-2(OAc)(4)-catalyzed reaction of alkyl 2-acyl-2-diazoacetates and dimethyl diazomalonate with methyl 2-bromo- and 2-chloro-3-phenyl-2H-azirine-2-carboxylates gives rise to electron-poor 4-halo-substituted (3E)-2-azabuta-1,3-dienes. Their formation proceeds with complete stereoselectivity via ring-opening of the intermediate azirinium ylide. 2-Azabuta-1,3-dienes with electron-withdrawing substituents at the 1,1,4-positions are stable compounds at room temperature, but are in equilibrium with cyclic valence isomers, 2,3-dihydroazetes, at elevated temperatures. (C) 2012 Elsevier Ltd. All rights reserved.
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