Configurational assignment to dl and meso sulfides, sulfoxides, and sulfones

Meyers, Cal Y.; Malte, A. M.

doi:10.1021/ja01036a052

Cited by 7 publications

(1 citation statement)

References 2 publications

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“…Bordwell and coworkers reported that the epimerization of -methylbenzyl sulfone in methanol gave a mixture consisting of 55.6% mp 140°i somer and 44.4% mp 89°i somer,10 to which Meyers and Malte assigned the meso and: dl configuration, respectively. 11 The difference between the ratio of ethers obtained by epimerization of -methylbenzyl sulfone and that of bis(aphenylethyl) ether may depend on two factors, i.e., the existence of the sulfonyl group in -methylbenzyl sulfone and the difference in the bond length between the C-S and C-0 bond. However, the notable stability of the dl isomer compared to meso isomer in bis(a-phenylethyl) ether is not well explained only on the basis of these factors.…”

Section: Discussionmentioning

confidence: 99%

Epimerization of Bis(α-phenylethyl) Ether and 2-Octyl α-Phenylethyl Ether

Akiyama¹,

Horie²,

Tokura³

1975

J. Org. Chem.

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Epimerization of bis(a-phenylethyl) ether and 2-octyl -phenylethyl ether catalyzed by boron trifluoride etherate was investigated in aprotic solvents. Bis(a-phenylethyl) ether gave a mixture consisting of 89.0% dl and 11.0% meso isomers in carbon tetrachloride and a mixture consisting of 78.8% dl and 21.2% meso isomers in liquid sulfur dioxide. On the other hand, 2-octyl -phenylethyl ether gave a mixture consisting of 58.7% three and 41.3% erythro isomers in the former solvent and a mixture consisting of equal amounts of threo and erythro isomers in the latter.

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Section: Discussionmentioning

confidence: 99%

Epimerization of Bis(α-phenylethyl) Ether and 2-Octyl α-Phenylethyl Ether

Akiyama¹,

Horie²,

Tokura³

1975

J. Org. Chem.

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Three‐Membered Rings Containing Sulfur

Zoller¹

1983

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Recognition and assignment of meso and dl diastereomers: Dimethyl α,α′‐Dibromopimelate and N‐benzyl‐2,6‐dicarbomethoxypiperidine

Solladié‐Cavallo

Bouchet²,

Wermuth³

1983

Org. Magn. Reson.

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The assignment of meso and dl diastereomers is carried out by NMR analysis of the signals due to the methylene protons in two simple cases, namely, dimethyl a,a'-dibromopimelate (as an acyclic compound) and N-benzyl-2,6-dicarbomethoxypiperidine (as a cyclic compound). In the case of the heterocyclic compound, an naa* hyperconjugative interaction between the CH bond (Y to the heteroatom and the lone pair of the heteroatom can be used, and leads to the same assignment.

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Configurational assignment to dl and meso sulfides, sulfoxides, and sulfones

Cited by 7 publications

References 2 publications

Epimerization of Bis(α-phenylethyl) Ether and 2-Octyl α-Phenylethyl Ether

Epimerization of Bis(α-phenylethyl) Ether and 2-Octyl α-Phenylethyl Ether

Three‐Membered Rings Containing Sulfur

Recognition and assignment of meso and dl diastereomers: Dimethyl α,α′‐Dibromopimelate and N‐benzyl‐2,6‐dicarbomethoxypiperidine

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