NON CONCERTED PATHWAY IN THE GENERATION OF DEHYDROARENES BY THERMAL DECOMPOSITION OF DIARYLIODONIUM CARBOXYLATES.

Article abstract of DOI:10.1016/S0040-4020(01)85138-3

1,3-Dehydrobenzene, 1,4-dehydrobenzene 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 C6H4CO2 for m- and p-benzyne and C10H6CO2 for 2,3-naphthalyne 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.