Photochemical reactions of acyl iodides with aryl halides View Full Text


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Article Info

DATE

2013-01

AUTHORS

M. G. Voronkov, N. N. Vlasova, L. I. Belousova, A. V. Vlasov, T. I. Vakul’skaya, G. F. Prozorova, S. S. Khutsishvili

ABSTRACT

Photochemical reactions of acyl iodides RC(O)I (R = Me, Ph) with aryl halides, fluoro-, chloro-, and bromobenzenes, 1,4-dibromobenzene, 2- and 3-bromotoluenes, and 4-bromo-1,2-dimethylbenzene, were studied. Acetyl iodide reacted with chloro- and bromobenzenes and 1,4-dibromobenzene according to the exchange pattern to give iodobenzene and 1,4-diiodobenzene, respectively. No halogen exchange was observed in the reactions of acetyl iodide with fluorobenzene and hexafluorobenzene. Benzoyl iodide failed to react with chloro- and brombenzene under UV irradiation but underwent polycondensation with formation of black nonfusible oligomers which were found to possess paramagnetic and semiconducting properties. Ultraviolet irradiation of a mixture of MeCOI with 2- or 3-bromotoluene, as well as with 4-bromo-1,2-dimethylbenzene, also led to the formation of polymeric products as a result of polycondensation of aryl iodides formed initially via replacement of bromine by iodine. Irradiation of benzoyl iodide in 2- or 3-bromotoluene involved recombination of benzoyl radicals to give benzil as the only product. More... »

PAGES

17-21

References to SciGraph publications

  • 2008-06. Synthesis of symmetric α-diketones in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2006-02. Acyl iodides in organic synthesis: VIII. Reactions with amino acids in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2009-11. Expected and unexpected photochemical reactions of acyl iodides in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 2008-11. Acyl iodides in organic synthesis: XII. Reactions with organosilicon amines in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
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    http://scigraph.springernature.com/pub.10.1134/s1070428013010041

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    http://dx.doi.org/10.1134/s1070428013010041

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