On the Fluxional Behavior of Dess-Martin Periodinane: A DFT and 17O NMR Study.

Luca Fusaro; Michel Luhmer; Giovanni Cerioni; Francesca. Mocci

doi:10.1021/jo901841v

On the Fluxional Behavior of Dess-Martin Periodinane: A DFT and 17O NMR Study.

Luca Fusaro, Michel Luhmer, Giovanni Cerioni, Francesca. Mocci

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Résumé

The structure and dynamics of the Dess-Martin periodinane, an I(V) iodobenzene compd. widely used in org. synthesis as a mild oxidant, were studied by a combined 17O NMR and DFT calcns. approach. The results show that a degenerate [1,3] sigmatropic shift of iodine between the two oxygen atoms of each of the three acetoxy groups occurs in soln. The energy barrier of this process depends on the position of the acetoxy group with respect to the iodoxolone ring and is much lower than the energy barrier obsd. for similar I(III) compds. [on SciFinder(R)]

langue originale	Anglais
Pages (de - à)	8818-8821
Nombre de pages	4
journal	Journal of Organic Chemistry
Volume	74
Numéro de publication	22
Les DOIs	https://doi.org/10.1021/jo901841v
Etat de la publication	Publié - 2009
Modification externe	Oui

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title = "On the Fluxional Behavior of Dess-Martin Periodinane: A DFT and 17O NMR Study.",

abstract = "The structure and dynamics of the Dess-Martin periodinane, an I(V) iodobenzene compd. widely used in org. synthesis as a mild oxidant, were studied by a combined 17O NMR and DFT calcns. approach. The results show that a degenerate [1,3] sigmatropic shift of iodine between the two oxygen atoms of each of the three acetoxy groups occurs in soln. The energy barrier of this process depends on the position of the acetoxy group with respect to the iodoxolone ring and is much lower than the energy barrier obsd. for similar I(III) compds. [on SciFinder(R)]",

keywords = "Dess Martin periodinane fluxional behavior oxygen NMR spectroscopy DFT",

author = "Luca Fusaro and Michel Luhmer and Giovanni Cerioni and Francesca. Mocci",

year = "2009",

doi = "10.1021/jo901841v",

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T1 - On the Fluxional Behavior of Dess-Martin Periodinane: A DFT and 17O NMR Study.

AU - Fusaro, Luca

AU - Luhmer, Michel

AU - Cerioni, Giovanni

AU - Mocci, Francesca.

PY - 2009

Y1 - 2009

N2 - The structure and dynamics of the Dess-Martin periodinane, an I(V) iodobenzene compd. widely used in org. synthesis as a mild oxidant, were studied by a combined 17O NMR and DFT calcns. approach. The results show that a degenerate [1,3] sigmatropic shift of iodine between the two oxygen atoms of each of the three acetoxy groups occurs in soln. The energy barrier of this process depends on the position of the acetoxy group with respect to the iodoxolone ring and is much lower than the energy barrier obsd. for similar I(III) compds. [on SciFinder(R)]

AB - The structure and dynamics of the Dess-Martin periodinane, an I(V) iodobenzene compd. widely used in org. synthesis as a mild oxidant, were studied by a combined 17O NMR and DFT calcns. approach. The results show that a degenerate [1,3] sigmatropic shift of iodine between the two oxygen atoms of each of the three acetoxy groups occurs in soln. The energy barrier of this process depends on the position of the acetoxy group with respect to the iodoxolone ring and is much lower than the energy barrier obsd. for similar I(III) compds. [on SciFinder(R)]

KW - Dess Martin periodinane fluxional behavior oxygen NMR spectroscopy DFT

U2 - 10.1021/jo901841v

DO - 10.1021/jo901841v

M3 - Article

SN - 0022-3263

VL - 74

SP - 8818

EP - 8821

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

On the Fluxional Behavior of Dess-Martin Periodinane: A DFT and 17O NMR Study.

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