Synthesis and stability of cyclic α-hydrogen nitroxides

Hila Toledo; Michal Amar; Sukanta Bar; Mark A. Iron; Natalia Fridman; Boris Tumanskii; Linda J.W. Shimon; Mark Botoshansky; Alex M. Szpilman

doi:10.1039/c5ob01443c

Synthesis and stability of cyclic α-hydrogen nitroxides

Hila Toledo, Michal Amar, Sukanta Bar, Mark A. Iron, Natalia Fridman, Boris Tumanskii, Linda J.W. Shimon, Mark Botoshansky, Alex M. Szpilman

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

Nitroxides (nitroxyl radicals) hold a unique place in science due to their stable radical nature. We have recently reported the first design concept providing a general solution to the problem of designing and preparing monocyclic α-hydrogen nitroxides. The initial studies were limited to aryl derivatives. We now report a wider study showing that alkyl substituents may be employed as well. In addition, we report several additional examples of aryl substituents and reveal some of the structural limitations with regard to nitroxide stability as a function of the α-carbon substituent.

Original language	English
Pages (from-to)	10726-10733
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	43
DOIs	https://doi.org/10.1039/c5ob01443c
State	Published - 2015
Externally published	Yes

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title = "Synthesis and stability of cyclic α-hydrogen nitroxides",

abstract = "Nitroxides (nitroxyl radicals) hold a unique place in science due to their stable radical nature. We have recently reported the first design concept providing a general solution to the problem of designing and preparing monocyclic α-hydrogen nitroxides. The initial studies were limited to aryl derivatives. We now report a wider study showing that alkyl substituents may be employed as well. In addition, we report several additional examples of aryl substituents and reveal some of the structural limitations with regard to nitroxide stability as a function of the α-carbon substituent.",

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AU - Toledo, Hila

AU - Amar, Michal

AU - Bar, Sukanta

AU - Iron, Mark A.

AU - Fridman, Natalia

AU - Tumanskii, Boris

AU - Shimon, Linda J.W.

AU - Botoshansky, Mark

AU - Szpilman, Alex M.

PY - 2015

Y1 - 2015

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AB - Nitroxides (nitroxyl radicals) hold a unique place in science due to their stable radical nature. We have recently reported the first design concept providing a general solution to the problem of designing and preparing monocyclic α-hydrogen nitroxides. The initial studies were limited to aryl derivatives. We now report a wider study showing that alkyl substituents may be employed as well. In addition, we report several additional examples of aryl substituents and reveal some of the structural limitations with regard to nitroxide stability as a function of the α-carbon substituent.

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JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 43

ER -

Synthesis and stability of cyclic α-hydrogen nitroxides

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