DIAZONIUM CARBOXYLATES

The salts of -halo acids cyclize in ionizing media to oxetan-2-ones, as do -diazonium carboxylates (64HC(19-2)787). Thietanes are obtained analogously (Section... 

Reaction of anthranilic acid (o-aminobenzoic acid) with HN02 and H2SO4 yields a diazonium salt that can be treated with base to yield a neutral diazonium carboxylate. 

See related diazonium carboxylates See other diazonium salts... 

Wilcox, C. F. et al., J. Amer. Chem. Soc., 1984, 106, 7196 It is more sensitive to thermal decomposition than other diazonium carboxylates, and will decompose readily when inadequate stirring, large scale or excessively rapid diazotisation produces too large a temperature rise. There is significant potential for violent eruption of suspensions, or detonation of the filtered solid, and all recommended precautions should be used. 

See 2-Carboxy-3,6-dimethylbenzenediazonium chloride See other DIAZONIUM CARBOXYLATES... 

See entry HIGH RATE DECOMPOSITION See related diazonium carboxylates... 

The product should be used immediately because it deteriorates slowly at room temperature. It is freed of tetrahydrofuran by washing with the solvent to be used in subsequent reactions and transferred as a slurry in that solvent (cf. procedure B). Traces of water, if present, do not appear to interfere with subsequent reactions of diazonium carboxylates, as observed in the submitters laboratory. 

ARENEDIAZONIUM OXIDES, DIAZONIUM CARBOXYLATES DIAZONIUM PERCHLORATES, DIAZONIUM SULFATES DIAZONIUM SULFIDES AND DERIVATIVES DIAZONIUM TETRAHALOBORATES, DIAZONIUM TRIIODIDES... 

Markl, Lieb and Martin were also able to add arynes 112 to 2.4,6-tiiphenyl-X -phosphorins the yields are better with 2.4.6-tri-tert-butyl-X -phosphorin. Here again 1,4 addition takes place with the formation of the 1-phosphabarfelenesiii. The arynes were generated either from 2-fluorophenylmagnesium bromide or penta-chlorophenyl-lithium. The reaction of the more nucleophilic 2.4.6-tri-tert-butyl-X -phosphorin with benzene-diazonium carboxylate also leads to 1,4 addition. The structure of the benzo-phosphabarrelenes 113a-d is supported by analytical and spectroscopic data (Table 16). 

---