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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 RM, Corfield PW, Annabi M, Regan J, Speina K, DiProperzio A, Ciaccio JA, Capitani JF - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: 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.The chains are linked by a second C-H⋯π inter-action, forming sheets parallel to the bc plane.

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Affiliation: Department of Chemistry and Biochemistry, Manhattan College, 4513 Manhattan College Pkwy, Bronx NY 10471, USA.

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⋯π 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⋯π inter-action, forming sheets parallel to the bc plane.

No MeSH data available.


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The mol­ecular structure of the title compound, (2), with atom labeling. Displacement ellipsoids are drawn at the 50% probability level. One of the H atoms on the methyl group C10 was omitted for clarity.
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fig1: The mol­ecular structure of the title compound, (2), with atom labeling. Displacement ellipsoids are drawn at the 50% probability level. One of the H atoms on the methyl group C10 was omitted for clarity.

Mentions: The mol­ecular structure of the title compound, (2), is illus­trated in Fig. 1 ▸. The dioxolane five-membered ring has a twist configuration on bond O1—C2, with atoms O1 and C2 at distances of 0.314 (4) and −0.330 (3) Å above and below the plane through atoms O3/C4/C5. The dioxolane ring has bond angles and distances that are within ca 3σ (using the larger s.u. values from the reported structures) of the values found in published X-ray structures (see for example: Rao & Hong Chan, 2014 ▸; Jones et al., 1998 ▸). The planes of the two phenyl substituents on the dioxolane ring are inclined to one another by 44.67 (13)°. They and the di­phenyl­ethyl substituent are all cis to one another, in equatorial positions. The phenyl rings of the di­phenyl­ethyl substituent are inclined to one another by 68.16 (12)°. There is an intra­molecular C—H⋯π inter­action present involving one of the di­phenyl­ethyl rings (C91–C96) and an H atom of the phenyl ring in position 4 of the dioxolane ring (Table 1 ▸).


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 RM, Corfield PW, Annabi M, Regan J, Speina K, DiProperzio A, Ciaccio JA, Capitani JF - Acta Crystallogr E Crystallogr Commun (2015)

The mol­ecular structure of the title compound, (2), with atom labeling. Displacement ellipsoids are drawn at the 50% probability level. One of the H atoms on the methyl group C10 was omitted for clarity.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645051&req=5

fig1: The mol­ecular structure of the title compound, (2), with atom labeling. Displacement ellipsoids are drawn at the 50% probability level. One of the H atoms on the methyl group C10 was omitted for clarity.
Mentions: The mol­ecular structure of the title compound, (2), is illus­trated in Fig. 1 ▸. The dioxolane five-membered ring has a twist configuration on bond O1—C2, with atoms O1 and C2 at distances of 0.314 (4) and −0.330 (3) Å above and below the plane through atoms O3/C4/C5. The dioxolane ring has bond angles and distances that are within ca 3σ (using the larger s.u. values from the reported structures) of the values found in published X-ray structures (see for example: Rao & Hong Chan, 2014 ▸; Jones et al., 1998 ▸). The planes of the two phenyl substituents on the dioxolane ring are inclined to one another by 44.67 (13)°. They and the di­phenyl­ethyl substituent are all cis to one another, in equatorial positions. The phenyl rings of the di­phenyl­ethyl substituent are inclined to one another by 68.16 (12)°. There is an intra­molecular C—H⋯π inter­action present involving one of the di­phenyl­ethyl rings (C91–C96) and an H atom of the phenyl ring in position 4 of the dioxolane ring (Table 1 ▸).

Bottom Line: 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.The chains are linked by a second C-H⋯π inter-action, forming sheets parallel to the bc plane.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry and Biochemistry, Manhattan College, 4513 Manhattan College Pkwy, Bronx NY 10471, USA.

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⋯π 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⋯π inter-action, forming sheets parallel to the bc plane.

No MeSH data available.


Related in: MedlinePlus