Methyl 2,4-dinitro-6- phenyl carbonate

Of the carboxylic acid esters the most important are isopropyl 2-i-butyl-4,6-dinitrophenyl carbonate (dinobuton, 8), methyl 2,4-dinitro-6-(l-ethylhexyl)phenyl carbonate (9a) and methyl 2,4-dinitro-6-(l-propylpentyl)phenyl carbonate (9b). The mixture of the two latter compounds has been introduced under the name dinocton-6 (9) (Pianka and Polton, 1963 Pianka and Smith, 1965). 

Dinocton is the isomeric mixture of 2,4-dinitro-6-octylphenyl methyl carbonate and 2,6-dinitro-4-octylphenyl methyl carbonate, in which the octyl group may be present in the form of 3 isomers, as for dinocap. In general, two active substances are present, one being dinocton-4, which is a mixture of mainly 2,6-dinitro-4-(l-ethylhexyOphenyl methyl carbonate (32) and 2,6-dinitro-4-(l-propylpentyl)phenyl methyl carbonate (33), with an acute oral value of460 mg/kg and a fungicidal... 

Primary alkyl phenyl tellurides undergo elimination to form terminal olefins in high yields on treatment with an excess of iV-chloro-iV-sodio-4-methyl-benzenesulphonamide (chloramine-T) in refluxing THF/ ufc-Dinitro compounds and /3-nitrosulphones are converted into olefins via free-radical elimination processes on treatment with tributyltin hydride in the presence of catalytic quantities of azobis(isobutyronitrile) (AIBN). Elimination from the dinitro compounds shows no stereocontrol by contrast, elimination from /3-nitrosulphones is highly stereoselective, e.g. (26)- (27), presumably because elimination from the intermediate radical is faster than rotation about the central carbon-carbon bond. 

---