99295-58-6Relevant articles and documents
High-pressure Synthesis, Structures, and Conformational Properties of Some Derivatives of 7-Azabicycloheptane. X-Ray Determination of endo-10-Benzoyl-4-phenyl-4,10-diazatricyclo2,6>dec-8-ene-3,5-dione and exo-10-Acetyl-4-phenyl-4,10-diazatricyclo2,6>decane-....
Drew, Michael G. B.,George, Adrian V.,Isaacs, Neil S.,Rzepa, Henry S.
, p. 1277 - 1284 (2007/10/02)
The syntheses, using pressures up to 1.4 GPa, and the properties of Diels-Alder adducts of some N-acylated pyrroles are described.Both exo and endo adducts may be obtained and purified and are, in general, unstable with respect to the retro reaction.Progress towards a general synthesis of the 7-azabicycloheptane system is described.Structures of two of the adducts, those between N-phenylmaleimide (2b) and N-benzoylpyrrole (1a) and the dihydro adduct of (2b) with N-acetylpyrrole (1b), have been determined by X-ray crystallographic analysis.Examination of these structures by means of 1H n.m.r. temperature-dependent spectra and nuclear Overhauser effect differences confirm that conformational isomerism is due to restricted rotation about the amide C-N bond, the energy barrier, 70 kJ mol-1, being similar to that in acyclic amides.
