Influence des effets orbitalaires sur l'équilibre conformationnel des sucres à insaturation terminale de configuration E

Tronchet, J. M. J.; Tho, Nguyen Xuan

doi:10.1016/s0008-6215(00)84134-8

Cited by 28 publications

(4 citation statements)

References 27 publications

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“…The orbital phase predictions were in good agreement with the experimental observations [8,9]. Tronchet and Xuan [8] concluded that the ac conformations of the glycenoses (e.g.…”

Section: Conformational Stabilitiessupporting

confidence: 79%

“…4c). The predictions were con®rmed by (1,2,7,8,13,14,19, and 20) calculated by ab initio molecular orbital methods. In the chloro derivatives, the calculated relative stabilities were in good agreement with the prediction for the b-substituted molecules, but not for the a-substituted molecules.…”

Section: Resultsmentioning

confidence: 80%

“…The orbital phase theory was readily applied to the cyclic molecules (7,8,13, and 14). The sp conformations in the acyclic molecules correspond to the (pseudo)equatorial conformations where the C·H bond preferentially interacts with the p bond.…”

Section: Conformational Stabilitiesmentioning

confidence: 99%

“…Tronchet and Xuan [8] concluded that the ac conformations of the glycenoses (e.g. 25) and alkenes having the general formula RCH(OR)CH CHX are favored when X is an electron donating group.…”

Section: Conformational Stabilitiesmentioning

confidence: 99%

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Orbital phase control of the conformations of α- and β-substituted enamines and vinyl ethers

Inagaki

Ohashi

1999

Theoretical Chemistry Accounts: Theory, Computation, and Modeli

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The conformational stabilities of the a-and b-substituted enamines and vinyl ethers were predicted by orbital phase theory and con®rmed by ab initio molecular orbital calculations. Cyclic interaction significantly occurs among the nonbonding orbital n Y for the lone pair on the hetero atom Y (N in the enamines or O in the ethers), the p and p* orbitals of the C¸C bond, and the r C-H or r* C-X orbitals on the substituent CH 2 X. The cyclic -n Y -p-r C-H -p*-interaction is favored by the orbital phase continuity in the a-substituted molecules, while the cyclic -n Y -p-r* C-X -p*-interaction is favored in the b-substituted molecules. The most stable conformation was then predicted to be synperiplanar or (pseudo)equatorial in the a-substituted molecules and anticlinical or (pseudo)axial in the b-substituted molecules.

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“…The orbital phase predictions were in good agreement with the experimental observations [8,9]. Tronchet and Xuan [8] concluded that the ac conformations of the glycenoses (e.g.…”

Section: Conformational Stabilitiessupporting

confidence: 79%

Section: Resultsmentioning

confidence: 80%

Section: Conformational Stabilitiesmentioning

confidence: 99%

Section: Conformational Stabilitiesmentioning

confidence: 99%

See 2 more Smart Citations

Orbital phase control of the conformations of α- and β-substituted enamines and vinyl ethers

Inagaki

Ohashi

1999

Theoretical Chemistry Accounts: Theory, Computation, and Modeli

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Nouveaux exemples d'acétonides d'aldéhydosucres furanniques

Tronchet¹,

Gentile²,

Bonenfant³

et al. 1979

Helvetica Chimica Acta

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Analogues de la showdomycine à activité antitumorale

Tronchet

Gentile

1979

Helvetica Chimica Acta

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A series of 3-glycosylidenesuccinimides (3) and 3-glycosylidene-I-phenylsuccinimides (5) have been prepared in good yields using a Wittig reaction. In each case, the preponderant, or even the exclusive, isomer formed was E. As expected I ) Dtrivts C-glycosyliques XXXVII; 36e communication: [I]. Utilisation d'ylures de phosphore en chimie des sucres XXIX; 28e communication: [2]. La matitre de cette communication constitue une partie de la Thtse de Doctorat 6s Sciences de M. Bernard Gentile [3]. 35 '

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Influence des effets orbitalaires sur l'équilibre conformationnel des sucres à insaturation terminale de configuration E

Cited by 28 publications

References 27 publications

Orbital phase control of the conformations of α- and β-substituted enamines and vinyl ethers

Orbital phase control of the conformations of α- and β-substituted enamines and vinyl ethers

Nouveaux exemples d'acétonides d'aldéhydosucres furanniques

Analogues de la showdomycine à activité antitumorale

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