Nucleophilic Ring Opening of Cyclic Sulfites -- a Convenient Method for Selective Functionalisation of 1,2-Diols.

Nymann, Kirsten; Svendsen, John S.; Magnusson, Göran; Huang, Man Shun Soon; Anthonsen, T.; Pati, Hari N.; Bisht, Kirpal S.; Parmar, Virinder S.; Francis, George W.

doi:10.3891/acta.chem.scand.48-0183

Cited by 13 publications

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“…( R,R ) - (+)-4,5-Diphenyl-1,3-dioxolanone (6a): 29 yield 85%; mp 110−112 °C (for (± ) - 6a lit . mp 110−111 °C); [α] D = +66 ( c = 1.05, CHCl 3 ); 1 H NMR δ 5.45 (s, 2H), 7.4 (m, 10H); 13 C NMR δ 85.34, 126.05, 129.23, 129.78, 134.88, 154.02.…”

Section: Methodsmentioning

confidence: 99%

Induction of Cholesteric Mesophases by Simple Cyclic Derivatives of p,p‘-Disubstituted 1,2-Diphenylethane-1,2-diols: Importance of Shape and Polarizability Effects

et al. 1999

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A systematic study of the cholesteric induction in nematic solvents (MBBA and E7) by some cyclic derivatives of unsubstituted and p,p'-disubstituted-1,2-diphenylethane-1,2-diols shows that the values of the twisting power are significantly dependent on the nature of the link connecting the two oxygen atoms and on the nature of the p,p'-substituents. This result has been interpreted considering that the nature of the bridge affects the overall molecular shape and the p,p'-substituents affect both the molecular polarizability and shape. This investigation points out that the polarizability of the solute and the solvent is the main parameter in determining the value of the twisting power while electrostatic arene-arene interactions contribute to a less extent. It has been also observed that solutes having the same structure and the same absolute configuration can induce cholesteric helix of opposite sign depending on the substituent on the aromatic ring. This finding indicates that configurational assignments by cholesteric induction are reliable only if high values of twisting power are measured.

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Section: Methodsmentioning

confidence: 99%

Induction of Cholesteric Mesophases by Simple Cyclic Derivatives of p,p‘-Disubstituted 1,2-Diphenylethane-1,2-diols: Importance of Shape and Polarizability Effects

et al. 1999

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“…13 Likewise, cyanation of the cyclic sulfite of 1-phenyl-1,2-ethanediol with tetraethylammonium cyanide gives the desired 3-hydroxy-3-phenylpropanenitrile in 65% yield. 14 By way of contrast, the reaction of aliphatic cyclic sulfites with NaCN is reported to give the corresponding diols. Also aromatic cyclic sulfites and cyclic sulfite of 1,2cyclohexanediol fail to react with NaCN under reflux in DMF.…”

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confidence: 99%

“…The cyclic sulfites derived from glycerol react with NaCN to give the corresponding cyanide derivative, only in the presence of tetrabutylammonium chloride . Likewise, cyanation of the cyclic sulfite of 1-phenyl-1,2-ethanediol with tetraethylammonium cyanide gives the desired 3-hydroxy-3-phenylpropanenitrile in 65% yield . By way of contrast, the reaction of aliphatic cyclic sulfites with NaCN is reported to give the corresponding diols.…”

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confidence: 99%

A Novel Stereospecific Synthesis of Glycosyl Cyanides from 1,2-O-Sulfinyl Derivatives

2004

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[reaction: see text] An efficient synthesis of 1,2-trans-glycosyl cyanides via 1,2-O-sulfinyl monosaccharides is described. Such S(N)2-type displacements at the anomeric center are stereospecific and are best performed with sodium cyanide in the presence of ytterbium triflate. Significantly, the resulting 1,2-trans-glycosyl cyanides have a free hydroxyl group at C-2 ready for further modification.

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Synthesis of Cyclic Sulfite Diesters and their Evaluation as Sulfur Dioxide (SO₂) Donors

2020

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Although sulfur dioxide (SO2) finds widespread use in the food industry as its hydrated sulfite form, a number of aspects of SO2 biology remain to be completely understood. Of the tools available for intracellular enhancement of SO2 levels, most suffer from poor cell permeability and a lack of control over SO2 release. We report 1,2‐cyclic sulfite diesters as a new class of reliable SO2 donors that dissociate in buffer through nucleophilic displacement to produce SO2 with tunable release profiles. We provide data in support of the suitability of these SO2 donors to enhance intracellular SO2 levels more efficiently than sodium bisulfite, the most commonly used SO2 donor for cellular studies.

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Nucleophilic Ring Opening of Cyclic Sulfites -- a Convenient Method for Selective Functionalisation of 1,2-Diols.

Cited by 13 publications

References 0 publications

Induction of Cholesteric Mesophases by Simple Cyclic Derivatives of p,p‘-Disubstituted 1,2-Diphenylethane-1,2-diols: Importance of Shape and Polarizability Effects

Induction of Cholesteric Mesophases by Simple Cyclic Derivatives of p,p‘-Disubstituted 1,2-Diphenylethane-1,2-diols: Importance of Shape and Polarizability Effects

A Novel Stereospecific Synthesis of Glycosyl Cyanides from 1,2-O-Sulfinyl Derivatives

Synthesis of Cyclic Sulfite Diesters and their Evaluation as Sulfur Dioxide (SO₂) Donors

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Nucleophilic Ring Opening of Cyclic Sulfites -- a Convenient Method for Selective Functionalisation of 1,2-Diols.

Cited by 13 publications

References 0 publications

Induction of Cholesteric Mesophases by Simple Cyclic Derivatives of p,p‘-Disubstituted 1,2-Diphenylethane-1,2-diols: Importance of Shape and Polarizability Effects

Induction of Cholesteric Mesophases by Simple Cyclic Derivatives of p,p‘-Disubstituted 1,2-Diphenylethane-1,2-diols: Importance of Shape and Polarizability Effects

A Novel Stereospecific Synthesis of Glycosyl Cyanides from 1,2-O-Sulfinyl Derivatives

Synthesis of Cyclic Sulfite Diesters and their Evaluation as Sulfur Dioxide (SO2) Donors

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Synthesis of Cyclic Sulfite Diesters and their Evaluation as Sulfur Dioxide (SO₂) Donors