2.4- Dinitrobenzenediazonium chloride

The rearrangement has been extended to other 4-substituted benzofuroxans of type 61, giving 62 i30-i32. although in no ease to date has the benzofuroxan been isolated, they are presumed intermediates in the formation of 63 and 64 from 5-dimethylaminobenzo-furoxan with 2,4-dinitrobenzenediazonium chloride and nitrous acid, respectively, and of 66 from 6, 68 from 67,and 70 from 69.132... 

ProUem 23.18 Beozenediazonium chloride couples with phenol, but not with the less reactive anisole. 2,4>Dinitrobenzenediazonium chloride, however, couples with anisole 2,4,6-trinitrobenzenediazonium chloride even couples with the hy o-carbon mesitylene (1,3,5-trimethylbenzene). (a) How can you account for these differences in behavior (b) Would you expectp-toluenediazonium chloride to be more or less reactive as a coupling reagent than benzenediazonium chloride ... 

Dinitrobenzenediazonium 2-oxide, 2080 2,4-Dinitrobenzenesulfonyl chloride, 2093 Dinitrogen oxide, 4739... 

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