Journal of the Chemical Society. Perkin transactions I p. 2456 - 2463 (1981)
Update date:2022-08-04
Topics:
Ramsden, Christopher A.
Formation of dibenzo-p-dioxins by the pyrolysis of 2-halogenophenoxides does not appear to involve intermediate benzoxirens.Thermal self-condensation to potassium 2-bromo-5-nitrophenoxide (1b) gave a mixture of 2,7- and 2,8-dinitrobenzo-p-dioxins (6d) and (6e).The mechanism of formation of the 2,8-isomer (6e) is shown to involve Smiles rearrangement of potassium 2-(2-bromo-5-nitrophenoxy)-5-nitrophenoxide (9a).Further examples of Smiles rearrangements of 2-aryloxy-5-nitrophenoxides and an attempted synthesis of the tribenzo
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