31009-94-6Relevant academic research and scientific papers
Unexpected formation of new bicyclic γ-lactams by dimerization of α-chloroacetoacetanilides
Han, Minsoo,Nam, Kee-Dal,Hahn, Hoh-Gyu,Shin, Dongyun
, p. 5217 - 5219 (2008/12/20)
Novel and unusual dimerization reaction of α-chloroacetoacetanilide under basic reaction condition to give structurally unique 6-oxa-3-azabicyclo[3.1.0]hexane was described.
Synthesis and structural assignment of oxanilo-N-arylhydrazonoyl chlorides
Frohberg, Petra,Drutkowski, Guntram,Wagner, Christoph
, p. 1654 - 1663 (2007/10/03)
Oxanilo-N-arylhydrazonoyl chlorides have been prepared from appropriate N-aryl-2-chloro-3-oxobutanamides by the Japp-Klingemann reaction. The structures of the title compounds have been established in the solid state by single-crystal X-ray structure determination and IR spectroscopy, and in solution by IR, UV, and 1H and 13C NMR spectroscopy. The results indicate that the hydrazonoyl chloride moiety adopts the (Z)-configured form. In the crystal, intramolecular hydrogen bonds generally exist between the chloride function and the hydrazone hydrogen atom, and also between the amide hydrogen atom and the double-bonded nitrogen atom of the hydrazone moiety. In solution, this intramolecular hydrogen bonding could not be detected. In compounds with an ortho-chloro-substituted NH-aryl moiety, however, the chlorine atom is involved in hydrogen bonding to the NH hydrogen atom both in the crystal and in solution. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
Structure elucidation of N-aryl-2-chloro-3-oxobutanamides with respect to intra- and intermolecular hydrogen bonding
Frohberg, Petra,Drutkowski, Guntram,Wagner, Christoph,Lichtenberger, Olaf
, p. 13 - 14 (2007/10/03)
In general, N-aryl-2-chloro-3-oxobutanamides form in solid state an intermolecular hydrogen bond between the anilide hydrogen and the anilide carbonyl oxygen of a neighbouring molecule, which is disrupted in solution. An intramolecular association could not be detected.
