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

Literature Information

Publication Date 2019-03-27
DOI 10.1039/C9OB00640K
Impact Factor 3.876
Authors

Zhongwei Zhu, Alexander M. Genaev


View Original

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.

Related Literature

The transformation from amorphous iron phosphate to sodium iron phosphate in sodium-ion batteries

Yao Liu, Yirong Zhou, Junxi Zhang, Shuojiong Xu

2015-07-28 Paper

DOI: 10.1039/C5CP02059J

Novel porphyrin-preparation, characterization, and applications in solar energy conversion

Jianfeng Lu, Hao Li, Shuangshuang Liu, Yu-Cheng Chang, Hui-Ping Wu, Eric Wei-Guang Diau, Mingkui Wang

2016-02-04 Paper

DOI: 10.1039/C5CP05658F

Specific ion modulated thermoresponse of poly(N-isopropylacrylamide) brushes

Ben A. Humphreys, Joshua D. Willott, Timothy J. Murdoch, Grant B. Webber, Erica J. Wanless

2016-01-28 Paper

DOI: 10.1039/C5CP07468A

Partitioning of mobile ions between ion exchange polymers and aqueous salt solutions: importance of counter-ion condensation

Jovan Kamcev, Michele Galizia, Francesco M. Benedetti, Eui-Soung Jang, Donald R. Paul, Benny D. Freeman, Gerald S. Manning

2016-01-19 Paper

DOI: 10.1039/C5CP06747B

A novel synthetic strategy for magnetite-type compounds. A combined experimental and DFT-computational study

Luigi Cigarini, Davide Vanossi, Claudio Fontanesi

2015-07-08 Paper

DOI: 10.1039/C5CP01852H

Multiscale modeling of the trihexyltetradecylphosphonium chloride ionic liquid

Sten Sarman, Bin Li, Aatto Laaksonen

2015-07-27 Paper

DOI: 10.1039/C5CP02586A

Unusual Mn coordination and redox chemistry in the high capacity borate cathode Li7Mn(BO3)3

Christopher Eames, Stephen M. Wood, M. Saiful Islam

2015-07-29 Paper

DOI: 10.1039/C5CP02711J

Binding properties of pendimethalin herbicide to DNA: multispectroscopic and molecular docking approaches

Irshad Ahmad, Ajaz Ahmad, Masood Ahmad

2016-02-10 Paper

DOI: 10.1039/C5CP07351K

You might also like

Compound Q&A

What is 1-(2,4,6-Trifluorophenyl)ethanol (CAS: 1250113-83-7)?

1-(2,4,6-Trifluorophenyl)ethanol is an organic compound with the CAS number 1250...

1250113-83-71-(2,4,6-Trifluoroph...
Compound Q&A

Is 1-(2,4-Dimethoxybenzyl)-4-(hydroxymethyl)-2-pyrrolidinone (CAS: 919111-34-5) safe?

1-(2,4-Dimethoxybenzyl)-4-(hydroxymethyl)-2-pyrrolidinone (CAS: 919111-34-5) is ...

919111-34-51-(2,4-Dimethoxybenz...
Compound Q&A

What are the physical and chemical properties of (7S,15R)-6β,15-Diacetoxy-7α,20-epoxy-7-hydroxykaura-2,16-dien-1-one (CAS: 51419-51-3)?

(7S,15R)-6β,15-Diacetoxy-7α,20-epoxy-7-hydroxykaura-2,16-dien-1-one is a crystal...

51419-51-3(7S,15R)-6β,15-Diace...
Compound Q&A

What regulatory guidelines apply to rac-ethyl (1r,4r)-4-hydroxycyclohexane-1-carboxylate, trans (CAS: 3618-04-0)?

The compound rac-ethyl (1r,4r)-4-hydroxycyclohexane-1-carboxylate, trans (CAS: 3...

3618-04-0rac-ethyl (1r,4r)-4-...
Compound Q&A

What is the market or research trend for 2-(2,4-Difluorophenoxy)-3-nitropyridine (CAS: 175135-62-3)?

The market for 2-(2,4-Difluorophenoxy)-3-nitropyridine (CAS: 175135-62-3) is cur...

175135-62-32-(2,4-Difluoropheno...
Compound Q&A

What are the main uses of 6-Diazo-5-oxo-L-norleucine (CAS: 157-03-9)?

The main uses of 6-Diazo-5-oxo-L-norleucine (CAS: 157-03-9) include research in ...

157-03-96-Diazo-5-oxo-L-norl...
Compound Q&A

What precautions should be taken when handling 2-Aminoethyl-mono-amide-DOTA-tris(tBu ester) (CAS: 173308-19-5)?

When handling 2-Aminoethyl-mono-amide-DOTA-tris(tBu ester) (CAS: 173308-19-5), i...

173308-19-52-Aminoethyl-mono-am...
Compound Q&A

How is 5-Methylimidazo[1,2-a]pyridine-3-carbaldehyde (CAS: 178488-37-4) typically synthesized?

5-Methylimidazo[1,2-a]pyridine-3-carbaldehyde (CAS: 178488-37-4) can be synthesi...

178488-37-45-Methylimidazo[1,2-...
Compound Q&A

Are there alternatives to 2,4,6-Trihydroxyisophthalaldehyde (CAS: 4396-13-8) in synthesis?

There are alternative reagents that can be used in the synthesis of 2,4,6-Trihyd...

4396-13-82,4,6-Trihydroxyisop...
Compound Q&A

What is (2Z)-3-(5-Fluoro-1H-indol-3-yl)-2-sulfanylacrylic acid (CAS: 179461-52-0)?

(2Z)-3-(5-Fluoro-1H-indol-3-yl)-2-sulfanylacrylic acid is a chemical compound wi...

179461-52-0(2Z)-3-(5-Fluoro-1H-...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.