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The mechanism of radical production from the reaction of N,N-dimethylaniline with benzoyl peroxide.

✍ Scribed by William A. Pryor; William H. Hendrickson Jr.

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
238 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

A&S?-RACT

The Jteaction be&en dimQh&anihnQ-dg and benzoye pecoxidc given an invQ5SQ kinetic iho.tope Q66ect 06 0.93, implying that mdicab ptimDnalriey UAbQ 6tom dQcompooition 06 Ph-CO-0-rf[Me)2Ph and not 6tom Qk?Qc.iXOn ~h.k~&j~~.

Many reactions that give products that can be rationalized by traditional ionic reaction mechanisms have been found in recent years to involve radical processes under some conditions. In particular, nucleophiles can react with suitable substrates either by the familiar SN2 reaction or by a radical-mediated process Initiated by an electron transfer (ET) reactlon.2 In recent years, a number of groups have studied the reactions of nucleophiles with peroxides in particular, since peroxides generally give products in an irreversible step upon either one-or two-electron transfer processes.3

The first peroxide-nucleophile reaction that was examined is that between N,N-dimethylaniline (DMA) and benzoyl peroxide (BPO),4 a reaction that continues to be 3. (a> (b) Cc> Cd) (e) (f)

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Menu-R~pheny~pohpki~o~oni1TI)/-imidazo~e ctiaeyzen the PoLunounhi Rope keirction 06 dub&&&d N,N-dimtihy1aniene N-axideo to give mititieh ud N-demeth&a&d and N-deoxygenatcd ptoducti . E~~ec\_.t 06 nubnmueti on the tinowe numbch and Rhe JUL& ofj the demtihylatioa to Ahe deoxygenation, and otheh oboema