Crystal structures of (E)-5-(4-methyl-phen-yl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis(phenyl-ethyn-yl)cyclo-butane-1,2-di-yl]bis-(pyridin-2-yl-methanone)

Abstract

Recrystallization of (E)-5-phenyl-1-(pyridin-2-yl)pent-2-en-4-yn-1-one at room temperature from ethyl-ene glycol in daylight afforded [3,4-bis-(phenyl-ethyn-yl)cyclo-butane-1,2-di-yl)bis-(pyridin-2-yl-methanone], C₃₂H₂₂N₂O₂ (3), while (E)-5-(4-methyl-phen-yl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one, C₁₇H₁₃NO (2), remained photoinert. This is the first experimental evidence that pentenynones can be photoreactive when fixed in nearly coplanar parallel positions. During the photoreaction, the bond lengths and angles along the pentenyne chain changed significantly, while the disposition of the pyridyl ring towards the keto group was almost unchanged. The cyclo-butane ring adopts an rctt conformation.

Keywords: crystal structure; cyclo­butane derivatives; photoreaction; vinyl ketones with acetyl­ene fragment.