Author:
Thomm E. W. C. W.,Wayman M.
Abstract
Various secondary amides have been N-chlorinated, at high and at low pH. The reactivity of the chlorinating reagents with all the amides investigated was found to have the sequence[Formula: see text]The substituent groups R1 and R2 of the amide [Formula: see text] were found to have large effects on the rate of chlorination. With the three molecular chlorinating agents, the reactivity of the amides was found to be in the order[Formula: see text]With hypochlorite ion the reverse order of reactivity was observed. These results are discussed and reaction mechanisms proposed. It is proposed that, when a hypochlorite ion is a chlorinating agent, the primary reaction is hydrogen bond formation between the amido hydrogen and the hypochlorite oxygen atom, but that the donation of electrons from the amido N to the Cl atom is the primary reaction with the molecular chlorinating agents.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
40 articles.
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