Substitution in 1-phenylpyrazole

Khan, Misbahal Ain (1962) Substitution in 1-phenylpyrazole. Masters thesis, Memorial University of Newfoundland.

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Abstract

A study of the nuclear substitution of 1-phenylpyrazole by the radicals liberated from thermal decomposition of benzoyl peroxide has been undertaken, with the object of testing the predictions of molecular-orbital calculations. Gas-liquid chromatographic analysis of the reaction products showed that the three 1-biphenylylpyrazoles and 1,3-diphenylpyrazole were present, and the isomer ratios were evaluated. There was no evidence for the presence of 1,4- or 1,5-diphenylpyrazole. -- Some nuclearbenzoyloxylation occurs in addition to phenylation, and a preliminary examination of the reaction products was made. In other preliminary work, the reactions occurring when benzoyl peroxide decomposes in 1-methylpyrazole and in 1-phenylpyrrole were examined. -- Certain electrophilic substitutions (bromination and nitration) of 1-phenylpyrazole and 1-p-biphenylylpyrazole have been studied. It has been found possible to effect changes in the orientation of substitution by varying the reaction conditions, and an explanation for this behaviour is suggested.

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