Electron impact induced cyclization of

ortho-cyclopropylphenylacetamides and benzamides. Prognosis for a similar reaction in solution

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Eur. J. Mass Spectrom. 4, 55 - 61 (1998)

Electron impact induced cyclization of ortho-cyclopropylphenylacetamides and benzamides. Prognosis for a similar reaction in solution

A.T. Lebedev,^* N.K. Karakhanova and S.S. Mochalov
Organic Chemistry Department, Moscow State University, Moscow, Russia 119899.
N. Tretyakova and R. Hass
Department of Environmental Science and Engineering, University of North Carolina at Chapel Hill, NC 27559, USA.

ABSTRACT:

The electron impact and collision-induced dissociation spectra of N-(ortho-cyclopropylphenyl)acetamide (1), N-(ortho-cyclopropylphenyl)benzamide (2), N-(ortho-cyclopropylphenyl)bromoacetamide (3), N-[ortho-(1-methylcyclopropyl)phenyl]benzamide (4) and N-[ortho-(1-methylcyclopropyl)phenyl]acetamide (5) were studied. The molecular ions of these compounds were shown to undergo cyclization into the corresponding 3-substituted 1-ethyl-1H-2,4-benzoxazines (610). 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 confirmed that the bromine-containing derivative 8 is the major product from the reaction of compound 3 with sulfuric acid.

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