The mechanism of the Friedel-Crafts reaction of 1-benzenesulfonyl-2-bromomethylethyleneimine with benzene
Koehler, Walter Robert
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When 1-benzenesulfonyl-2-bromomethylethyleneimine, I, is treated with aluminum chloride in benzene the only identifiable product, isolated in 30 percent yield, is N-(3,3-diphenylpropyl)benzenesulfonamide, II. In earlier work on the mechanism of this reaction, several compounds had been tested by subjecting them to the same conditions as those employed in the conversion of 1- benzenesulfonyl-2-bromomethyleneimine, I, to N-(3,3-diphenylpropyl)- benzenesulfonamide, II, and noting whether or not the same product, II, was obtained. The compounds so tested were a) 2-benzenesulfonamido-1,3-diphenylpropane, b) 2-benzenesulfonamido- 1-bramo-3-phenylpropane, c) 1-benzenesulfonamido-2- benzylethyleileimine, and d) N-( cinnamyl)-benzenesulfonamide. In the present work a fifth compound, 1-benzenesulfonyl-2-phenyl- · azetidine, XXVIII; was also tested in this manner. Only the last of these compounds, the 1-benzenesulfonyl-2-phenylazetidine, yielded II when subjected to the Friedel-Crafts conditions used in the original reaction. Moreover the yield of II was more than twice as large as the best yield reported in the production of II from I. [TRUNCATED]
Thesis (Ph.D.)--Boston University
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