Dibenzyl sulfone, derivative

The sulfonyl group is a key feature in the preparation of the unusually substituted dithiin sulfone (174) from dibenzyl sulfone. The acidic a-protons are abstracted with sodium hydride and the carbanionic intermediates react with carbon disulfide. The reaction is quenched with methyl iodide to give (174) in 17% yield (73BSF637). Another multisubstituted dithiin (175) is available from the reaction of diphenylthiirene dioxide with the ylide (176) (Scheme 21) but again the yield is low. However, the reaction is of particular interest in so far as the product mixture also contains a derivative of the rare oxathiin nucleus. Indeed of the three products isolated the oxathiin sulfone (177) is formed in marginally the highest yield (73BCJ667). 

Odier diemistries that have been employed as photoadd generators in chemically amplified resist compositions include imino sulfonates (22), 4-nitro-benzenesulfonic add derivatives (23), disulphone compounds 24), sulfonyl substituted diazomethanes (25), dibenzyl sulfones 26), and aryl-bu-trichloro-methyl-s-triazines (27). 

With the sodium derivative of benzyl alcohol, dibenzyl ether was obtained in 63% yield, accompanied by 24% of A-benzylimidazole. Formation of the latter compound results from the reaction of the benzyl sulfonate with imidazol sodium in competition with the second step of the ether synthesis (b). 

The following compounds are used as inhibitors in acid solutions amines, amino-imidazolines, amino- and nitrophenols, aminotriazole, aldehydes, bezothiazol, dibenzyl sulfoxide, dithiophos-phoric acids, guanidine derivatives, ureas, phosphonium salts, sulfonium salts, sulfonic acids, thio-ethers, thioureas, and thiocarbanoyl disulfides. Amino alcohols, aminobenzimidazole, benzoates, quinoline derivatives, cinnamates, fatty amines, polyether amines, silicates, and triazoles are used as inhibitors in neutral or weakly alkaline solutions, while for strongly alkaline solutions, aldehydes and fatty amines are used. 

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