79807-55-9Relevant articles and documents
The Smiles Rearrangement of 2-Aryloxy-5-nitrophenoxides. Attempted Routes to Benzoxirens and Tribenzotrioxonins
Ramsden, Christopher A.
, p. 2456 - 2463 (2007/10/02)
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 tribenzotrioxonin derivatives (16) are described.