Triazines sulfonated, oxidation with

Oxidation of triazine herbicides with chlorine and chlorine dioxide has been widely studied [105-108]. In the case of sulfur-containing triazines, oxidation occurs mainly via cleavage of the weakened R-S-CH3 bond rather than by addition of chlorine. Reactions of S-triazines with chlorine are faster than with chlorine dioxide, and form sulfoxide, sulfone, and a sulfone hydrolysis product. Chlorination with chlorine dioxide only produced sulfoxide [108]. Lopez et al. identified the formation of sulfonate esters during the chlorination of ametryn and terbutryn [106, 107]. Triazine DBFs identified by Brix et al. exhibited higher toxicities than the parent compounds [105]. Similar to triazines, clethodim, a cyclohexanedione herbicide, is oxidized by hypochlorite and chloramines to clethodim sulfoxide and then to sulfone [109]. 

Oxidation of 3,5-bis(methylthio)-l,2,4-triazines (81) with potassium permanganate afforded the 3-monosulfones (241) which could be hydrolyzed to 5-methylthio-l,2,4-triazin-3-ones (242) (69BSF3670). 6-Benzyl-3-thioxo-l,2,4-triazin-5-one (243) with potassium permanganate afforded the 6-benzoyl-3-sulfonic acid (244) (67BSF2551). Similarly, 5-amino-... 

The reaction of 3-methoxy-1,2,4-triazine 1-oxide 20 with the carbanion generated from chloromethyl phenyl sulfone proceeds as the vicarious nucleophilic substitution (VNS) of hydrogen (Scheme 1, path B) via addition of the carbanion at position 5 of the heterocycle. Following base-induced elimination of HCl and protonation, 3-methoxy-5-phenylsulfonyl-1,2,4-triazine 4-oxides 65 result (88LA627). 

At the same time, the reaction of 1,2,4-triazine 4-oxides 55 with the anion of chloromethyl phenyl sulfone affords 5-(l-chloro-l-phenylmethyl)-l,2,4-triazines 66. In this case, autoaromatization of the a -adducts proceeds by the deoxygenative... 

Oxidation of the partially saturated derivative of the thiazolo[4,3-c][l,2,4]triazine ring system 115 was studied by Stoodley et al. <1999J(P1)1067>. Reaction of 115 with w-chloroperbenzoic acid gave rise to the cyclic sulfone 116 in poor yield (28%). 

The actual formation of hyperbranched material proceeds during the polymerization of 3,5-difluoro-4 -hydroxydiphenyl sulfone in the presence of 3,4,5-trifluorophenylsulfonyl benzene or tris(3,4,5-trifluorophenyl)phos-phine oxide as a core molecule. Cyclic oUgomers formed dining this polymerization contribute to a low-molecular-weight polymer ranging from 3400 to 8400 Dalton. A triazin-based AB2 monomer has also been described. This monomer is shown in Figure 7.8. A hyperbranched aromatic poly(ether sulfone) with sulfonyl chloride terminal groups has been prepared by the polycondensation of 4,4 -(m-phenylenedioxy)-bis-(benz-enesulfonyl chloride). The polymerization was carried out in nitrobenzene at 120°C for 3 h in the presence of a catalytic amount of FeCls. ... 

---