Charge Transfer Complexes of Isoindolines with Tetracyanoethylene and its Analogous

N‐Arylisoindolines 1a‐c reacted with (2,4, 7‐trinitro‐9H‐fluoren‐9‐ylidene)propanedinitrile (A) in pyridine with admission of air via a net α‐H‐atom abstraction and formation of [3‐(2‐aryl‐3‐arylimino‐2,3‐dihydro‐ 1H‐isoindol‐1‐ylidene)‐2‐aryl‐2,3‐dihydro‐1H‐isoindol‐1‐ylidene]propanedinitriles 2a‐c, N‐[2‐aryl‐3‐(2‐aryl‐3‐arylimino‐2,3‐dihydro‐1H‐isoindolyl‐1‐idene)‐2,3‐dihydro‐1H‐isoindol‐1‐ylidene]arenamines 3a, b, N, N'‐[2‐aryl‐1H‐isoindole‐1,3(2H)‐diylidene]bisarenamines 4a, b and N‐arylphthalimides 5a‐c in moderate yields. 2,4,7‐Trinitro‐9‐fluorenone as well as one reduction product each of the latter and of A, namely compounds 6 and 7, respectively, are also found. The structure of 2b has been unambiguously confirmed by an X‐ray crystal structure analysis. A rationale for the conversions observed is presented. These involve dehydrogenation and oxidative couplings of 1a‐c as well as transfer of N‐aryl fragment from 1a‐c to intermediate products.

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Reaction of (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile with N-arylisoindolines

Döpp

Hassan

El‐Din

et al. 2006

Tetrahedron

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Charge Transfer Complexes of Isoindolines with Tetracyanoethylene and its Analogous

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New tandem cyclo‐ and/or addition reactions between N‐arylisoindolines with benzyne and dimethyl acetylenedicarboxylate

New tandem cyclo‐ and/or addition reactions between N‐arylisoindolines with benzyne and dimethyl acetylenedicarboxylate

A novel reaction of (2a7‐trinito‐9H‐fluoren‐9‐ylidene)‐propanedinitrile with N‐arylisoindolines

Reaction of (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile with N-arylisoindolines

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