Synthesis of unsymmetrical N-(2-tert-butylphenyl)-N-(4-tert-butylphenyl)nitroxyl radical, the first stable diarylnitroxyl with vacant para-position

Oleg A. Levitskiy; Vyacheslav V. Sentyurin; Alexey V. Bogdanov; Tatiana V. Magdesieva

doi:10.1016/j.mencom.2016.11.026

Synthesis of unsymmetrical N-(2-tert-butylphenyl)-N-(4-tert-butylphenyl)nitroxyl radical, the first stable diarylnitroxyl with vacant para-position

Oleg A. Levitskiy
, Vyacheslav V. Sentyurin
, Alexey V. Bogdanov
, Tatiana V. Magdesieva^*

^*Corresponding author for this work

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

14 Citations (Scopus)

Abstract

The title compound, first example of a stable diarylnitroxyl with vacant para-position, was best synthesized by CuCl-assisted coupling of o-tert-butylnitrosobenzene and p-tert-butylphenylboronic acid followed by N-xidation of the thus obtained unsymmetrical diarylamine. ESR investigation showed that ortho-substituted aromatic ring is removed from the conjugation plane providing unusual stability of this radical.

Original language	English
Pages (from-to)	535-537
Number of pages	3
Journal	Mendeleev Communications
Volume	26
Issue number	6
DOIs	https://doi.org/10.1016/j.mencom.2016.11.026
Publication status	Published - 1 Nov 2016
Externally published	Yes

Funding

This work was supported by the Russian Science Foundation (project no. 16-13-10282). NMR parts of this work were supported by the M. V. Lomonosov Moscow State University ‘Program of Development’. We are grateful to D. Eremin for MS analysis; mass spectra were recorded in Department of Structural Studies, N. D. Zelinsky Institute of Organic Chemistry RAS.

All Science Journal Classification (ASJC) codes

General Chemistry

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10.1016/j.mencom.2016.11.026

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abstract = "The title compound, first example of a stable diarylnitroxyl with vacant para-position, was best synthesized by CuCl-assisted coupling of o-tert-butylnitrosobenzene and p-tert-butylphenylboronic acid followed by N-xidation of the thus obtained unsymmetrical diarylamine. ESR investigation showed that ortho-substituted aromatic ring is removed from the conjugation plane providing unusual stability of this radical.",

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AU - Sentyurin, Vyacheslav V.

AU - Bogdanov, Alexey V.

AU - Magdesieva, Tatiana V.

PY - 2016/11/1

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AB - The title compound, first example of a stable diarylnitroxyl with vacant para-position, was best synthesized by CuCl-assisted coupling of o-tert-butylnitrosobenzene and p-tert-butylphenylboronic acid followed by N-xidation of the thus obtained unsymmetrical diarylamine. ESR investigation showed that ortho-substituted aromatic ring is removed from the conjugation plane providing unusual stability of this radical.

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Synthesis of unsymmetrical N-(2-tert-butylphenyl)-N-(4-tert-butylphenyl)nitroxyl radical, the first stable diarylnitroxyl with vacant para-position

Abstract

Funding

All Science Journal Classification (ASJC) codes

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