132652-64-3Relevant academic research and scientific papers
THE REACTION OF QUINOXALINE- AND PHENAZINE-N-OXIDES WITH THIONYL CHLORIDE AND PARATOLUENESULFONYL CHLORIDE
Nasielski, J.,Heilporn, S.,Chauveheid, E.,Poppe, K.,Nasielski-Hinkens, R.
, p. 783 - 788 (2007/10/02)
2,3-Diphenylquinoxaline-N-oxide 1 with thionyl chloride gives only 5-chloro- and 6-chloroquinoxaline and very little deoxygenation.Phenazine-N5-oxide 2, in the same conditions, gives mainly 2-chlorophenazine and minor amounts of 1-chlorophenazine, but here deoxygenation is an important pathway.Freshly recrystallized para-toluenesulfonyl chloride gives a high chlorination-to-tosyloxylation ratio.All these results point to a variable ability of acid chlorides to yield homocycle chlorination or acyloxylation; this is confirmed by the observation that phenazine-N5-oxide and phosphoryl chloride give fair amounts of aryl phosphate.
