Volume 33, Issue 16
Isocyclic Compounds
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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.

A. P. Avdeenko

A. P. Avdeenko

Donbass State Macinebuild. Acad., Kramatorsk 184313, Ukraine

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A. L. Yusina

A. L. Yusina

Donbass State Macinebuild. Acad., Kramatorsk 184313, Ukraine

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L. M. Yagupol'skii

L. M. Yagupol'skii

Donbass State Macinebuild. Acad., Kramatorsk 184313, Ukraine

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First published: 22 May 2010

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)].

chemical structure image

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