ELECTRON-IMPACT INDUCED CYCLIZATION OF ORTHO-CYCLOPROPYLPHENYLACETAMIDES AND BENZAMIDES - PROGNOSIS FOR A SIMILAR REACTION IN SOLUTION

The electron impact and collision-induced dissociation spectra of N-(o rtho-cyclopropylphenyl)acetamide (1), N-(ortho-cyclopropylphenyl)benza mide (2), N-(ortho-cyclopropylphenyl)bromoacetamide (3), N-[ortho-(1-m ethylcyclopropyl)phenyl]benzamide (4) and N-[ortho-(1-methylcyclopropy l)phenyl]acetamide (5) were studied. The molecular ions of these compo unds were shown to undergo cyclization into the corresponding 3-substi tuted 1-ethyl-1H-2,4-benzoxazines (6-10), Following proposals made on the basis of mass spectrometry experiments, compound 7 was obtained by interaction of compound 2 with sulfuric acid. GC/MS experiments confi rmed that the bromine-containing derivative 8 is the major product fro m the reaction of compound 3 with sulfuric acid.