112302-03-1Relevant academic research and scientific papers
Schmidt reaction on camphor. Part I. Structure of the products
Hunter, Norman R.,Khan, M. Zafar,Marat, Kirk,El-Kabbani, Ossama A. L.,Delbaere, Louis T. J.
, p. 137 - 149 (2007/10/02)
A reinvestigation of the major product from the Schmidt reaction on camphor has led to the assignment of the structure as 1,9,9-trimethyl-3-oxo-2,8-diazabicyclononane (5).The structure has been established by high-field proton and carbon-13 nuclear magnetic resonance, as well as degradation to the imine ester 4.Confirmation of the structure of 5 was achieved by X-ray crystallography.Compound 5, C10H18N2O, crystallized in space group P21/a with a = 14.934(1) Angstroem, b = 10.973(1) Angstroem, c = 12.341(1) Angstroem, β = 92.0 deg, and Z = 8.The relatively rare cis amide linkage is present in the molecule.In addition to the amino amide 5, the Schmidt reaction on camphor leads to small amounts of the tetrazole 8 and the imine nitrile 9.
