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)

Recrystallization of ( )-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], C H N O ( ), while ( )-5-(4-methyl-phen-yl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one, C H N...

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Bibliographic Details
Published in:Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2020-02, Vol.76 (Pt 2), p.192-196
Main Authors: Ushakov, Ivan E, Odin, Ivan S, Gloukhov, Pavel A, Golovanov, Alexander A, Dorovatovskii, Pavel V, Vologzhanina, Anna V
Format: Article
Language:English
Subjects:
crystal structure
cyclobutane derivatives
photoreaction
Research Communications
vinyl ketones with acetylene fragment
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Summary:Recrystallization of ( )-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], C H N O ( ), while ( )-5-(4-methyl-phen-yl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one, C H NO ( ), 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 conformation.
ISSN:2056-9890
2056-9890
DOI:10.1107/S2056989020000055