The conjugate (E)- and (Z)-(4′-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4′-pyridylethenyl-4-phenyl-β-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4′-pyridylethenyl)-4-phenyl]-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono- and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge–transfer complexes with TCNE, TCNQ and TMPD.

中文翻译：

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π-扩展的共轭苯基乙炔。4-[（E）和（Z）-2-（4-乙烯基苯基）乙烯基]吡啶的合成。电荷转移复合物的二聚，季铵化和形成

共轭物（E）-和（Z）-（4'-吡啶基乙烯基）-4-苯基乙炔（E - 4和Z - 4）已通过两种不同的途径令人满意地制备：（a）通过4'-吡啶基乙烯基-的脱卤化氢4-苯基-β-氯乙烯; （b）通过对-（碘苄基）（三苯基）膦内酯与4-吡啶羧甲醛之间的维蒂希反应，E / Z异构体分离，并与2-甲基-丁-3-炔-2-醇交叉偶联消除。（Z）-4的Glaser氧化二聚化产生（Z，Z）-1,4-二[（4'-吡啶基乙烯基）-4-苯基] -buta-1,3-二炔，收率好，（Z，Z）-5。（E，E）-5通过在其N-甲基盐（E）-10存在下通过相转移氧化二聚来获得（E）-4。通过与碘甲烷季铵化获得共轭物（E，E）-5和（Z，Z）-5的单-和二-N-甲基化的盐。（Z，Z）-5 二甲基氮盐与TCNE，TCNQ和TMPD形成电荷转移复合物。