ChemInform Abstract: Activated Sterically Strained C=N Bond in N-Arylsulfonyl-p-quinonemono- and Diimines. Part 9. Synthesis and Reactions of N-Tosyl-2,3,5,6-tetramethyl-1,4-benzoquinonimine.
Abstract
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ChemInform Abstract
The preparation of title compound (VI) having an activated C=N bond and studies on its reactivity are described. Reactions of quinoneimine (VI) with azides and alcohols occur as 1,2-addition affording products with quinoid structure [cf. (IX), (XV), resp.], whereas reactions with aromatic amines furnish products of a 1,2-addition—elimination path [cf. (VIII)]. Moreover, an unusual combination of two simultaneous processes, i.e. 6,1- and 1,6-addition, is observed in reactions with arylsulfinic acids [→(XI)/(XII)].