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Non concerted pathways in the generation of dehydroarenes by thermal decomposition of diaryliodonium carboxylates.

✍ Scribed by S.V. Luis; F. Gaviña; P. Ferrer; V.S. Safont; M.C. Torres; M.I. Burguette

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
1011 KB
Volume
45
Category
Article
ISSN
0040-4020

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✦ Synopsis

and 2,3_dehydronaphthalene are generated in the thermal decomposition of appropriate diaryliodonium carboxylates as demonstrated by the use of the three phase test. Intermediate species C8H4C02 for m-and p-benzyne and ClgHgC02 for 2,3naphthalyne have been unambiguously trapped in the same way, showing how non-concerted processes are the main pathway for generation of arynic intermediates from those iodonium salts.

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Diphenyliodonium tetrafluoroborate and diphenyliodonium hexafluorophosphate have been found to generate u p to two equivalents of hydrogen fluoride per equivalent of the iodonium salt by pyrolysis at 239°C in the neat state and at 150°C in the presence of anisole or nitrobenzene. The formation of hy