Date of Graduation

1968

Document Type

Dissertation

Committee Chair

Denis W.H. MacDowell

Committee Member

Gabor B. Fodor

Committee Member

John H. Gruninger

Committee Member

Frederick J. Lotspeich

Abstract

In a study with variation of the ylid-nitrobenzene ratio and subsequent treatment with air, the optimum reaction conditions for the methylation of nitrobenzene with dimethyloxosulfonium ylid were found to be an 8-fold molar excess of methylid over nitrobenzene, and initial reaction for 15 minutes in an atmosphere of nitrogen, followed IX by passing air through the reaction mixture for 5 hours prior to work-up. With these experimental conditions the nitrotoluene yield was increased from 17$ to 40–50$, dialkylation was observed, and essentially no nitrobenzene was recovered.

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