Stereochemistry of 1,3-diheterocyclanes 4. Molecular and crystal structures of monosubstituted five-membered cyclic sulfites |
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Authors: | A A Bredikhin A T Gubaidullin D B Krivolapov Z A Bredikhina I A Litvinov |
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Institution: | (1) A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088 Kazan, Russian Federation |
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Abstract: | Racemic and enantiopure cis-and trans-4-(1-naphthyloxy)methyl-2-oxo-1,3,2-dioxathiolanes were studied by X-ray diffraction. The factors responsible for their crystal
packings were revealed. The conformation of the exocyclic fragment varies from synclinal to antiperiplanar depending on both
the local (cis-trans isomerism of the molecule) and external (homochiral/heterochiral environment) stereochemical factors. Data on the structures
of five-membered sulfites in crystals were generalized. It was concluded that the heterocycle has considerable conformational
flexibility.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1095–1102, July, 2006. |
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Keywords: | cyclic sulfites 1 3 2-dioxathiolanes chirality X-ray diffraction analysis conformational analysis crystal packing |
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