Santalova A. Synthesis, structure investigation and reaction ability of N-arylsulfenyl- and N-arylsulfinyl-1,4-benzoquinoneimines.

The object of investigation is the N-arylsulfеnyl- and N-arylsulfinyl-1,4-benzoquinonemonoimines, N,N’-bis(arylsulfenyl)- and N,N’-bis(arylsulfinyl)-1,4-benzoquinonediimines, N-chloro-1,4-benzoquinonemonoimines. The aim of investigation is to determine the dsrection of interaction of N-chloro-1,4-benzoquinonemonoimines with thiols, to develope the new methods of synthesis of N-arylsulfеnyl- and N-arylsulfinyl-1,4-benzoquinonemonoimines, to investigate their spatial structure and mechanism of Z,E-isomerization. The methods – the organic synthesis, the element analysis, the IR, NMR 1H, 13С spectroscopy and X-ray. The newness - the new N-arylsulfenyl-1,4-benzoquinonemonoimines have been obtasned in the reactions of arylthiols with N-chloro-1,4-benzoquinonemonoimines, and it has been established the addition of arylthiols proceeds to both either N-arylsulfenyl-1,4-benzoquinonemonoimines or N-chloro-1,4-benzoquinoneimines. The new method of synthesis of N-arylsulfinyl-1,4-benzoquinonemonoimines, which is the oxidation of N-arylsulfenyl-1,4-benzoquinonemono- and -diimines by m-chloroperbenzoic acid, has been developed. The mechanism of Z,E-isomerization of N-arylsulfenyl- and N-arylsulfinil-1,4-benzoquinonemonoimines have been investigated. It is established the interaction of N-arylsulfinyl-1,4-benzoquinonemonoimines with chlorid hydrogen and arylsulfinic acids proceeds through – addition of nucleofil and break of S–N bond; the direction of a reaction depends on ratio of speeds of these two processes. For the first time the interaction of N-arylsulfinyl-1,4-benzoquinonenimines with sodium azide has been established to proceed with formation of 2-azido-N-arylsulfenyl-1,4-benzoquinoneimines.