Abstract
AbstractThe synthesis and isolation is reported of five terminal aryl/biaryl‐butadiynes, Ar–C≡C–C≡CH, (5a–c, 10a and 10b) from 2‐methyl‐6‐aryl/biaryl‐hexa‐3,5‐diyn‐2‐ol precursors [Ar–C≡C–C≡C–C(Me)2OH; Ar = 2‐MeOC6H4, 3‐MeOC6H4, 4‐MeOC6H4, 2‐phenylpyridin‐5‐yl, 3‐phenylpyridin‐2‐yl, respectively]. The X‐ray crystal structures have been obtained for compounds 5c and 10a. Surprisingly, no ≡C–H···X (X = N or O) hydrogen bonds exist in the crystals of 5c and 10a. These structures illustrate the fact that ≡C–H···X hydrogen bonds are not always reliable tools for crystal engineering. Palladium‐catalysed cross‐coupling of 5c with 2‐iodopyrimidine gave the unsymmetrical 1,4‐diarylbutadiyne derivative 12; copper‐catalysed reactions of 5c and 10a with benzyl azide proceeded regioselectively to give alkynyltriazoles 13 and 14.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
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