Optically active 1,3-diethynylallenes (DEAs) were prepared by enantioselective Pd-mediated SN2′-type cross-coupling and their absolute configuration was determined by X-ray analysis. Addition of tetracyanoethene (TCNE) to donor-substituted DEAs affords novel 1,1,4,4-tetracyanobutadiene (TCBDs)-based charge-transfer chromophores in high yield. CD spectroscopy reveals strong chiral induction from the optically pure allene into the directly adjacent TCBD moieties.
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Alonso‐Gómez et al. (2008) studied this question.
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