Abstract
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-diazabicyclo[3.3.1]nonane (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) Å, b = 10.973(1) Å, c = 12.341(1) Å, β = 92.0°, 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.
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