Mechanistic investigation of superelectrophilic activation of 1,1′-bi-2-naphthols in the presence of aluminum halides

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Mechanistic investigation of superelectrophilic activation of 1,1′-bi-2-naphthols in the presence of aluminum halides. / Zhu, Zhongwei; Genaev, Alexander M.; Salnikov, George E. et al.

In: Organic and Biomolecular Chemistry, Vol. 17, No. 16, 17.04.2019, p. 3971-3977.

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

Author

Zhu, Zhongwei ; Genaev, Alexander M. ; Salnikov, George E. et al. / Mechanistic investigation of superelectrophilic activation of 1,1′-bi-2-naphthols in the presence of aluminum halides. In: Organic and Biomolecular Chemistry. 2019 ; Vol. 17, No. 16. pp. 3971-3977.

BibTeX

@article{4364106e56624bdcb162d91ad3144cc6,

title = "Mechanistic investigation of superelectrophilic activation of 1,1′-bi-2-naphthols in the presence of aluminum halides",

abstract = "7,7′-Dihydroxy-1,1′-bi-2-naphthol, as a result of superelectrophilic activation in the presence of an excess of aluminum halides, reacts with cyclohexane and benzene to yield 5,6,7,8,5′,6′,7′,8′-octahydro-7,7′-dioxo-bi-2-naphthol and its 5,5′-diphenyl derivative, respectively. In contrast, isomeric 6,6′-dihydroxy-1,1′-bi-2-naphthol does not react at all under the same reaction conditions, while the parent 1,1′-bi-2-naphthol (BINOL) reveals an alternative mode of behavior. The mechanistic aspects of these intriguing results are discussed on the basis of experimental and theoretical (DFT) study of the protonation and complexation properties of the starting BINOLs.",

keywords = "IONIC HYDROGENATION, BINOL, CYCLOHEXANE, ACID, NAPHTHALENEDIOLS, CONDENSATION, BENZENE",

author = "Zhongwei Zhu and Genaev, {Alexander M.} and Salnikov, {George E.} and Koltunov, {Konstantin Yu}",

note = "Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry.",

year = "2019",

month = apr,

day = "17",

doi = "10.1039/c9ob00640k",

language = "English",

volume = "17",

pages = "3971--3977",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "16",

}

RIS

TY - JOUR

T1 - Mechanistic investigation of superelectrophilic activation of 1,1′-bi-2-naphthols in the presence of aluminum halides

AU - Zhu, Zhongwei

AU - Genaev, Alexander M.

AU - Salnikov, George E.

AU - Koltunov, Konstantin Yu

PY - 2019/4/17

Y1 - 2019/4/17

N2 - 7,7′-Dihydroxy-1,1′-bi-2-naphthol, as a result of superelectrophilic activation in the presence of an excess of aluminum halides, reacts with cyclohexane and benzene to yield 5,6,7,8,5′,6′,7′,8′-octahydro-7,7′-dioxo-bi-2-naphthol and its 5,5′-diphenyl derivative, respectively. In contrast, isomeric 6,6′-dihydroxy-1,1′-bi-2-naphthol does not react at all under the same reaction conditions, while the parent 1,1′-bi-2-naphthol (BINOL) reveals an alternative mode of behavior. The mechanistic aspects of these intriguing results are discussed on the basis of experimental and theoretical (DFT) study of the protonation and complexation properties of the starting BINOLs.

AB - 7,7′-Dihydroxy-1,1′-bi-2-naphthol, as a result of superelectrophilic activation in the presence of an excess of aluminum halides, reacts with cyclohexane and benzene to yield 5,6,7,8,5′,6′,7′,8′-octahydro-7,7′-dioxo-bi-2-naphthol and its 5,5′-diphenyl derivative, respectively. In contrast, isomeric 6,6′-dihydroxy-1,1′-bi-2-naphthol does not react at all under the same reaction conditions, while the parent 1,1′-bi-2-naphthol (BINOL) reveals an alternative mode of behavior. The mechanistic aspects of these intriguing results are discussed on the basis of experimental and theoretical (DFT) study of the protonation and complexation properties of the starting BINOLs.

KW - IONIC HYDROGENATION

KW - BINOL

KW - CYCLOHEXANE

KW - ACID

KW - NAPHTHALENEDIOLS

KW - CONDENSATION

KW - BENZENE

UR - http://www.scopus.com/inward/record.url?scp=85064695674&partnerID=8YFLogxK

U2 - 10.1039/c9ob00640k

DO - 10.1039/c9ob00640k

M3 - Article

C2 - 30942805

AN - SCOPUS:85064695674

VL - 17

SP - 3971

EP - 3977

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 16

ER -

ID: 19647593