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Activated Sterically Strained C = N Bond in N-Arylsulfonyl-p-quinonemono- and Diimines: IX. Synthesis and Reactions of N-Tosyl-2,3,5,6-tetramethyl-1,4-benzoquinonimine
Authors:A P Avdeenko  A L Yusina  L M Yagupol'skii
Institution:(1) Donbass State Machinebuilding Academy, Kramatorsk, 84313, Ukraine;(2) Ukrainian National Academy of Sciences, Institute of Organic Chemistry, Kiev, Ukraine
Abstract:N-Tosyl-2'3'5'6-tetramethyl-1'4-benzoquinonimine as the other N-arylsulfonyl-1'4-benzo-quinonimines with an activated C = N bond reacts along 1'2-addition path with alcohols, sodium azideand along 1,2-addition-elimination path with aromatic amines. The higher activity of the C = N bond in theN-arylsulfonyl-1,4-benzoquinonimines is not due to the electronic character of the substituent attached to the ring (Cl, CH3) but to steric influence resulting in increase in the bond angle C = N-S.
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