Interaction of 1,3-diaxial sulfur atoms

Smissman, Edward E.; Diebold, James L.

doi:10.1021/jo01268a033

Cited by 3 publications

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“…The reaction of ketones 5a–c with 1,2-ethanedithiol in the presence of catalytic BF 3 ·OEt 2 afforded the corresponding bis-dithianes 6a–c in moderate to good yields [26] (Scheme 2). The reaction of diketone 5c also afforded the monoderivatised ketone 9 as a minor product.…”

Section: Resultsmentioning

confidence: 99%

Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

Jones¹,

Callejo²,

Slawin³

et al. 2016

Beilstein J. Org. Chem.

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2,2-Dimethyl-5-phenyl-1,1,3,3-tetrafluororocyclohexane has been prepared and characterised as an example of a facially polarised cyclohexane containing 1,3 related CF2 groups. The dipolar nature of the ring arises from the axial orientation of two of the C–F bonds pointing in the same direction, and set by the chair conformation of the cyclohexane. This electrostatic profile is revealed experimentally both in the solid-state (X-ray) packing of the rings and by solution (NMR) in different solvents. A computationally derived electrostatic profile of this compound is consistent with a more electronegative and a more electropositive face of the cyclohexane ring. This placing of CF2 groups 1,3 to each other in a cyclohexane ring is introduced as a new design strategy which could be applicable to the preparation of polar hydrophobic cyclohexane motifs.

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Section: Resultsmentioning

confidence: 99%

Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

Jones¹,

Callejo²,

Slawin³

et al. 2016

Beilstein J. Org. Chem.

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Preparation of the laevorotatory trans-(4S,6S)-4,6-dimethyl-1,3-dithiane and trans-(4S,6S)-4,6-dimethyl-1,3-oxathiane. An internal displacement of a secondary sulphonate leading to a cyclic thioacetal

et al. 1975

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The Reaction of 2-Ethoxy-1,3-oxathiolane with Carbonyl Compounds in the Presence of ZnCl2 or HgCl2

Tanimoto¹,

Jo²,

Sugimoto³

et al. 1981

Bulletin of the Chemical Society of Japan

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In the reaction of 2-ethoxy-1,3-oxathiolane with carbonyl compounds in the presence of ZnCl2 or HgCl2, it has been found that only the breaking of the endocyclic bond (C–O or C–S bond) occurs, while the breaking of the exocyclic C–O bond to give the 1,3-oxathiolan-2-ium ion is unfavorable. This behavior is different from that of 2-ethoxy-1,3-dithiolane, in which the breaking of the endocyclic C–S bond occurs by means of HgCl2 and the exocyclic C–O bond, by means of ZnCl2.

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Interaction of 1,3-diaxial sulfur atoms

Cited by 3 publications

References 0 publications

Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

Preparation of the laevorotatory trans-(4S,6S)-4,6-dimethyl-1,3-dithiane and trans-(4S,6S)-4,6-dimethyl-1,3-oxathiane. An internal displacement of a secondary sulphonate leading to a cyclic thioacetal

The Reaction of 2-Ethoxy-1,3-oxathiolane with Carbonyl Compounds in the Presence of ZnCl2 or HgCl2

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