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Crystal structure of 2?-(1,1-di-phenyl-eth-yl)-4-methyl-4?,5?-diphenyl-1,3-dioxolane: the result of a non-acid pinacol rearrangement.

ABSTRACT: The title compound, C30H28O2, was obtained during recrystallization of (±)-1,2-diphenyl-1,2-propane-diol in 1-butanol, from an unexpected non-acid-catalyzed pinacol rearrangement followed by acetal formation of the newly formed aldehyde with the diol. The tri-substituted dioxolane ring has a twist conformation on the C-O bond opposite the methyl-substituted C atom. There is an intra-molecular C-H?? inter-action present involving one of the di-phenyl-ethyl rings and an H atom of the phenyl ring in position 4 of the dioxolane ring. In the crystal, mol-ecules are linked by weak C-H?O hydrogen bonds, forming chains along [001]. The chains are linked by a second C-H?? inter-action, forming sheets parallel to the bc plane.

SUBMITTER: Kirchner RM 

PROVIDER: S-EPMC4645051 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Crystal structure of 2α-(1,1-di-phenyl-eth-yl)-4-methyl-4α,5α-diphenyl-1,3-dioxolane: the result of a non-acid pinacol rearrangement.

Kirchner Richard M RM   Corfield Peter W R PW   Annabi Michelle M   Regan John J   Speina Kevin K   DiProperzio Anthony A   Ciaccio James A JA   Capitani Joseph F JF  

Acta crystallographica. Section E, Crystallographic communications 20151003 Pt 11

The title compound, C30H28O2, was obtained during recrystallization of (±)-1,2-diphenyl-1,2-propane-diol in 1-butanol, from an unexpected non-acid-catalyzed pinacol rearrangement followed by acetal formation of the newly formed aldehyde with the diol. The tri-substituted dioxolane ring has a twist conformation on the C-O bond opposite the methyl-substituted C atom. There is an intra-molecular C-H⋯π inter-action present involving one of the di-phenyl-ethyl rings and an H atom of the phenyl ring i  ...[more]

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