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The conversion of azobenzenes to phenazines: A new molecular rearrangement
Author(s) -
Abramovitch R. A.,
Davis B. A.
Publication year - 1968
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570050610
Subject(s) - chemistry , azobenzene , reagent , ferrous , oxalate , chloride , photochemistry , medicinal chemistry , polymer chemistry , organic chemistry , molecule
When azobenzenes arc heated with ferrous oxalate or with a fused mixture of aluminum chloride and sodium chloride the corresponding phenazines are formed in low yield. Azobenzene itself is exceptional in giving benz[ c ]cinnoline with AlCl 3 ‐NaCl. Azoxybenzenes and ferrous oxalate give azobenzenes and some phenazines, while azoxybenzene itself also gives 2‐hydroxyazobenzene via a Wallach‐type rearrangement. The rearrangements are thought to occur at the surfaces of the reagent. No rearrangement to the phenazines occurs in the absence of the reagent.