179092-78-5Relevant academic research and scientific papers
Aziridination of α,β-unsaturated esters by (ethoxycarbonyl)nitrene
Carducci, Monica,Fioravanti, Stefania,Loreto, M. Antonietta,Pellacani, Lucio,Tardella, Paolo A.
, p. 3777 - 3778 (1996)
The reaction of α,β-unsaturated esters with (ethoxycarbonyl)nitrene, generated by α-elimination of NsONHCO2Et using CaO as a base in heterogeneous phase, allowed the preparation of aziridine-1,2-dicarboxylates (2a-e) in good isolated yields (57-72%). The same reaction does not take place using triethylamine instead of CaO, in homogeneous conditions.
Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
Pinho e Melo, Teresa M. V. D.,Cardoso, Ana L.,Rocha Gonsalves, Anto?nio M. D'A.
, p. 2345 - 2351 (2007/10/03)
The dehalogenation of 2-halo-3-phenyl-2H-azirine-2-carboxylates is described. Using sodium borohydride and tributyltin hydride 3-phenyl-2H-azirine-2-carboxylates were obtained in moderate yields. The synthesis of a new 2-bromo-2H-azirines with a chiral au
The Regioselectivity of the Ring Opening of 1-Activated or Nonactivated 2-Alkoxycarbonyl or 2-Cyanoaziridines by Carbanions of the Dicarbonyl Compounds
Bouayad, Zoheir,Chanet-Ray, Josette,Ducher, S.,Vessiere, Roger
, p. 1757 - 1768 (2007/10/02)
Ring opening of title compounds with alkyl malonates, acetylacetone, methyl acetylacetate, and malononitrile was studied.The regioselectivity of the opening depends on several facts.A phenyl group on C-3 favours C-3-N bond cleavage, whereas C-2-N bond cleavage is predominant with C-3-substituted or C-2-H aziridines.Cyanoaziridines are predominantly cleaved at C-3-N.The aziridine configuration at C-2 and C-3 is maintained during the cyclisation in pyrrolidones.
Synthesis of α-Halocinnamate Esters via Solvolytic Rearrangement of Trichloroallyl Alcohols
Kruper, William J.,Emmons, Albert H.
, p. 3323 - 3329 (2007/10/02)
Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-α-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement.Micharl addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides.The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.
