Stereochemical studies—XXVI

Mursakulov, I. G.; Guseinov, M. M.; Kasumov, N. K.; Зефиров, Н. С.; Samoshin, Vyacheslav V.; Chalenko, E. G.

doi:10.1016/0040-4020(82)85169-7

Cited by 10 publications

(4 citation statements)

References 48 publications

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“…Details of the syntheses of previously reported ketones 17 62 and 37 , in addition to acetals 7 , − , 11b , and 11c , , are provided as Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

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Nucleophilic Substitution Reactions of Sulfur-Substituted Cyclohexanone Acetals: An Analysis of the Factors Controlling Stereoselectivity

Billings

Woerpel

2006

J. Org. Chem.

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The reactions of cyclohexanone acetals substituted with thiophenyl groups (and other heteroatoms) at C-2 demonstrate the powerful influence that these substituents have on the stereoselectivity of nucleophilic substitution reactions. The trans selectivities of these reactions correlate with the behavior of the corresponding ketones. These experiments lend support to the possibility that the reactions of the acetals, which proceed via oxocarbenium ions, are operating under Felkin-Anh control.

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“…Details of the syntheses of previously reported ketones 17 62 and 37 , in addition to acetals 7 , − , 11b , and 11c , , are provided as Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

“…Nitrile 10. The standard cyanation procedure was followed with acetal 7 , − , Me 3 SiCN (0.198 mL, 1.50 mmol), and BF 3 · OEt 2 (0.056 mL, 0.45 mmol). GC and 1 H NMR spectroscopic analysis of the unpurified product detected only a single isomer was present.…”

Section: Methodsmentioning

confidence: 99%

Nucleophilic Substitution Reactions of Sulfur-Substituted Cyclohexanone Acetals: An Analysis of the Factors Controlling Stereoselectivity

Billings

Woerpel

2006

J. Org. Chem.

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“…In particular, 1-(OR), 1-(OR'), 2-(R") derivatives have atracted much attention because they are suitable for investigating different interactions. Zefirov and co-workers (3,4) showed that %-substituted propylene ketals usually prefer the axial orientation but this preference decreases as the polarity of the solvent increases. Ethylene ketals behave in almost the opposite direction except for OH and OCH:, derivatives.…”

Section: Introductionmentioning

confidence: 99%

“…Author to whom correspondence may be addressed. structure of complex systems (1)(2)(3)(4)(5)(6)(7). Conformational equilibria of 1,1,2 trisubstituted cyclohexanes have been studied (6) and the experimental AG values give direct information on the most stable conformations.…”

Section: Introductionmentioning

confidence: 99%

Solvent effect on the conformational behavior of substituted spiro[4.5]decanes and spiro[5.5]undecanes

Erdem¹,

Varnali²,

Avi̇yente³

et al. 1995

Can. J. Chem.

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Abstract:We studied the relatively complex polar systems 6-substituted-l,4-dioxospiro[4.5]decanes and 7-substituted-l,5-dioxospiro[5.5]undecanes with substituents X = CH,, F, C1, CN, OH, OCH,, and NOz. Solvent effects on theequilibrium have been analysed by means of a Self-Consistent-Reaction-Field model and the PM3 method. Complete geometry optimizations have been carried out for all the structures in the gas phase and in solution. For some substituents, a set of rotamers have been separately optimized. The discussion of the results is focussed on the effects arising from structural aspects and from steric and electrostatic interactions on the axial/equatorial relative stability. The role played by multipole moment is considered. In general, good agreement with available experimental data and with previous theoretical studies has been obtained. Though the use of semiempirical methods and simple solvent models prevents us from reaching definitive conclusions, this approach seems to be very useful in predicting the main role of solute-solvent interactions in conformational equilibria of complex systems for which ab initio calculations cannot be performed.

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Conformational analysis of 2-cyano-1,1-dihydroxyethane in solution

Avi̇yente

Varnali

Ruiz‐López

1996

J. Phys. Org. Chem.

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The conformational space of the 2-cyano-1,l-dihydroxyethane molecule was studied at the semi-empirical PM3 level and ab initio MP2/6-31G**//6-31G level in the gas phase and in a low-polarity medium. This system has been chosen as a model compound for 2-cyanocyclohexanone propylene and ethylene acetals. This has allowed the study of the role of polar groups on the relative conformation of two adjacent OH groups, which is of interest also in relation to the anomeric effect in carbohydrate chemistry. Solvent effects are taken into account using a continuum model with general cavity shapes,

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Stereochemical studies—XXVI

Cited by 10 publications

References 48 publications

Nucleophilic Substitution Reactions of Sulfur-Substituted Cyclohexanone Acetals: An Analysis of the Factors Controlling Stereoselectivity

Nucleophilic Substitution Reactions of Sulfur-Substituted Cyclohexanone Acetals: An Analysis of the Factors Controlling Stereoselectivity

Solvent effect on the conformational behavior of substituted spiro[4.5]decanes and spiro[5.5]undecanes

Conformational analysis of 2-cyano-1,1-dihydroxyethane in solution

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