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C–N bond formation followed by N–Cl bond breaking. One more and unexpected case of the formation of a hydroxamic group via heterolytic bond cleavage by Ivana Vinković Vrček; Viktor Pilepić; Stanko Uršić is a Chemistry article available to read on EtoBox.

What is C–N bond formation followed by N–Cl bond breaking. One more and unexpected case of the formation of a hydroxamic group via heterolytic bond cleavage about?

An unexpected and previously unknown reaction sequence in the interactions of the acyl halides with nitrosobenzenes, which involves carbon-nitrogen bond formation followed by heterolytic nitrogen-chlorine bond cleavage giving the corresponding unsubstituted N-phenylalkylhydroxamic acids (or N-phenylarylhydroxamic acids) and chlorine as the products has been observed. The kinetic and other evidence obtained suggest that the carbon-nitrogen bond formation is the consequence of a nucleophilic interaction of an N-phenylchlorohydroxylamine intermediate, formed in the first reaction step, with the acyl halide in the second step of the complex sequence, which leads to an N-acyl-N-chlorophenylhydroxylamine cation intermediate. The key reaction step involves the interaction of an N-acyl-N-chlorophenylhydroxylamine cation intermediate with chloride ion, which leads to the N-Cl heterolytic bond cleavage and the final formation of the hydroxamic group and a molecule of chlorine.

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Author

Ivana Vinković Vrček; Viktor Pilepić; Stanko Uršić

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

2004

Language

EN

Field

Chemistry (Physical Sciences)