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Acid-Catalyzed Versus Thermally Induced C1-C1′ Bond Cleavage in 1,1′-Bi-2-naphthol : An Experimental and Theoretical Study. / Genaev, Alexander M.; Shchegoleva, Lyudmila N.; Salnikov, George E. et al.

In: Journal of Organic Chemistry, Vol. 84, No. 11, 07.06.2019, p. 7238-7243.

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

Harvard

Genaev, AM, Shchegoleva, LN, Salnikov, GE, Shernyukov, AV, Shundrin, LA, Shundrina, IK, Zhu, Z & Koltunov, KY 2019, 'Acid-Catalyzed Versus Thermally Induced C1-C1′ Bond Cleavage in 1,1′-Bi-2-naphthol: An Experimental and Theoretical Study', Journal of Organic Chemistry, vol. 84, no. 11, pp. 7238-7243. https://doi.org/10.1021/acs.joc.9b00915

APA

Genaev, A. M., Shchegoleva, L. N., Salnikov, G. E., Shernyukov, A. V., Shundrin, L. A., Shundrina, I. K., Zhu, Z., & Koltunov, K. Y. (2019). Acid-Catalyzed Versus Thermally Induced C1-C1′ Bond Cleavage in 1,1′-Bi-2-naphthol: An Experimental and Theoretical Study. Journal of Organic Chemistry, 84(11), 7238-7243. https://doi.org/10.1021/acs.joc.9b00915

Vancouver

Genaev AM, Shchegoleva LN, Salnikov GE, Shernyukov AV, Shundrin LA, Shundrina IK et al. Acid-Catalyzed Versus Thermally Induced C1-C1′ Bond Cleavage in 1,1′-Bi-2-naphthol: An Experimental and Theoretical Study. Journal of Organic Chemistry. 2019 Jun 7;84(11):7238-7243. doi: 10.1021/acs.joc.9b00915

Author

Genaev, Alexander M. ; Shchegoleva, Lyudmila N. ; Salnikov, George E. et al. / Acid-Catalyzed Versus Thermally Induced C1-C1′ Bond Cleavage in 1,1′-Bi-2-naphthol : An Experimental and Theoretical Study. In: Journal of Organic Chemistry. 2019 ; Vol. 84, No. 11. pp. 7238-7243.

BibTeX

@article{5619c829d9734ae581573af063de674a,
title = "Acid-Catalyzed Versus Thermally Induced C1-C1′ Bond Cleavage in 1,1′-Bi-2-naphthol: An Experimental and Theoretical Study",
abstract = "Experiments show that 1,1′-bi-2-naphthol (BINOL) undergoes facile C1-C1′ bond cleavage under action of triflic acid at temperatures above 0 °C to give mainly 2-naphthol along with oligomeric material. CASSCF and MRMP//CASSCF computations have demonstrated unambiguously that this unusual mode of scission of the biaryl bond can occur in the C1,C1′-diprotonated form of BINOL via a mechanism involving homolytic cleavage prompted by the intramolecular electrostatic repulsion. These findings also provide insights into the mechanism of a comparatively easy thermal cleavage of BINOL, implying the intermediacy of its neutral diketo form.",
keywords = "HYDROGEN-TRANSFER, BINOL, THERMOLYSIS, EFFICIENT, RADICALS",
author = "Genaev, {Alexander M.} and Shchegoleva, {Lyudmila N.} and Salnikov, {George E.} and Shernyukov, {Andrey V.} and Shundrin, {Leonid A.} and Shundrina, {Inna K.} and Zhongwei Zhu and Koltunov, {Konstantin Yu}",
year = "2019",
month = jun,
day = "7",
doi = "10.1021/acs.joc.9b00915",
language = "English",
volume = "84",
pages = "7238--7243",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "11",

}

RIS

TY - JOUR

T1 - Acid-Catalyzed Versus Thermally Induced C1-C1′ Bond Cleavage in 1,1′-Bi-2-naphthol

T2 - An Experimental and Theoretical Study

AU - Genaev, Alexander M.

AU - Shchegoleva, Lyudmila N.

AU - Salnikov, George E.

AU - Shernyukov, Andrey V.

AU - Shundrin, Leonid A.

AU - Shundrina, Inna K.

AU - Zhu, Zhongwei

AU - Koltunov, Konstantin Yu

PY - 2019/6/7

Y1 - 2019/6/7

N2 - Experiments show that 1,1′-bi-2-naphthol (BINOL) undergoes facile C1-C1′ bond cleavage under action of triflic acid at temperatures above 0 °C to give mainly 2-naphthol along with oligomeric material. CASSCF and MRMP//CASSCF computations have demonstrated unambiguously that this unusual mode of scission of the biaryl bond can occur in the C1,C1′-diprotonated form of BINOL via a mechanism involving homolytic cleavage prompted by the intramolecular electrostatic repulsion. These findings also provide insights into the mechanism of a comparatively easy thermal cleavage of BINOL, implying the intermediacy of its neutral diketo form.

AB - Experiments show that 1,1′-bi-2-naphthol (BINOL) undergoes facile C1-C1′ bond cleavage under action of triflic acid at temperatures above 0 °C to give mainly 2-naphthol along with oligomeric material. CASSCF and MRMP//CASSCF computations have demonstrated unambiguously that this unusual mode of scission of the biaryl bond can occur in the C1,C1′-diprotonated form of BINOL via a mechanism involving homolytic cleavage prompted by the intramolecular electrostatic repulsion. These findings also provide insights into the mechanism of a comparatively easy thermal cleavage of BINOL, implying the intermediacy of its neutral diketo form.

KW - HYDROGEN-TRANSFER

KW - BINOL

KW - THERMOLYSIS

KW - EFFICIENT

KW - RADICALS

UR - http://www.scopus.com/inward/record.url?scp=85066959293&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.9b00915

DO - 10.1021/acs.joc.9b00915

M3 - Article

C2 - 31083942

AN - SCOPUS:85066959293

VL - 84

SP - 7238

EP - 7243

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 11

ER -

ID: 20530576