The mechanism of the Friedel-Crafts reaction of 1-benzenesulfonyl-2-bromomethylethyleneimine with benzene
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Abstract
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- ยท
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]
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Thesis (Ph.D.)--Boston University
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