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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 17
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Original Articles

Photo-Ritter Reaction of Arylmethyl Bromides in Acetonitrile

Nai-Min Bi Department of Chemistry, Joint Laboratory of Green Synthetic Chemistry, University of Science and Technology of China, Hefei, China
,
Ming-Guang Ren Department of Chemistry, Joint Laboratory of Green Synthetic Chemistry, University of Science and Technology of China, Hefei, China
&
Qin-Hua Song Department of Chemistry, Joint Laboratory of Green Synthetic Chemistry, University of Science and Technology of China, Hefei, ChinaCorrespondence[email protected]
Pages 2617-2623 | Received 10 Apr 2009, Published online: 05 Aug 2010
 
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Abstract

The photo-Ritter reaction of five arylmethyl bromides can occur in acetonitrile to give acetamides. The intermediates, carbocations, which are formed from subsequent electron transfer between the radical pairs generated from initial homolytic cleavage of the C–Br bond, are trapped by acetonitrile, and subsequent hydrolysis generates the corresponding acetamides.

ACKNOWLEDGMENT

We thank the National Natural Science Foundation of China (Grant Nos. 20972149 and 30870581).

Notes

a [Substrate] = 1 mM, determined by high-performance liquid chromatography (HPLC) directly on the crude product mixture.

b Irradiation wavelengths, which are maxima absorption peaks of arylmethyl bromides.

c Irradiation time.

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