Date of Award
6-1973
Document Type
Open Access
Degree Name
Masters of Science
Department
Chemistry
First Advisor
John Sowa
Language
English
Abstract
When dimethyl sulfoxide, ethyl bromide, and 5 mole-percent of ferric chloride are heated together, a yellow precipitate is formed. The product partially decomposes at 172 degrees, with evolution of gas. It is very soluble in water, but only slightly soluble in methanol. It contains 7.18% by weight of iron (III), suggesting a compound of high molecular weight or a mixture. It appears that a Friedel-Crafts alkylation of DMSO has taken place, perhaps giving an ethyldimethyloxosulfonium salt, however, the IR and NMR spectra do not substantiate this. The absence of alkoxydimethylsulfonium salts in the above reaction mixture has been demonstrated. An attempt to prepare ethyldimethyloxosulfonium iodide by reacting ethyl methyl sulfoxide with methyl iodide gave no precipitate. Addition of ferric chloride to this reaction mixture followed by heating gave a crystalline solid which showed only a singlet in the NMR.
Recommended Citation
Dean, Robert Wallace Jr., "Reactions of Alkyl Halides in Dimethyl Sulfoxide under Friedel-Crafts Conditions" (1973). Honors Theses. 2205.
https://digitalworks.union.edu/theses/2205
Rights Statement
