Base controlled diverse reactivity of allyl cyanide for synthesis of multi-substituted benzenes
Literature Information
Publication Date
2018-07-10
DOI
10.1039/C8OB01270A
Impact Factor
3.876
Authors
Pratik Yadav, Ranjay Shaw, Amr Elagamy, Abhinav Kumar, Ramendra Pratap
View Original
Abstract
A base controlled regioselective 1,6-cyanoallylation of suitably functionalized 2H-pyran-2-ones has been demonstrated for the synthesis of various multi-substituted benzenes through a tandem process. We observed that lithium hydroxide provides a major product from α-attack and a minor product from γ-attack of allyl cyanide, while the use of sodium hydride as a base exclusively provides the product by γ-attack of allyl cyanide. We have also performed NMR experiments to understand the mechanistic pathway. The structure of the compound was confirmed by single crystal X-ray analysis.
Related Literature
Surface-orientation- and ligand-dependent quenching of the spin magnetic moment of Co porphyrins adsorbed on Cu substrates
Md. Ehesan Ali, Matthias Bernien, Nino Hatter, Fabian Nickel, Lalminthang Kipgen, Christian F. Hermanns, Timo Bißwanger, Philip Loche, Benjamin W. Heinrich, Katharina J. Franke, Peter M. Oppeneer, Wolfgang Kuch
2020-05-18
Paper
DOI: 10.1039/D0CP00854K
Irreproducibility in the triboelectric charging of insulators: evidence of a non-monotonic charge versus contact time relationship
Jinyang Zhang, Chao Su, Fergus J. M. Rogers, Nadim Darwish, Michelle L. Coote, Simone Ciampi
2020-05-07
Paper
DOI: 10.1039/D0CP01317J
Fine structure in the solution state 13C-NMR spectrum of C60 and its endofullerene derivatives
George Razvan Bacanu, Gabriela Hoffman, Michael Amponsah, Maria Concistrè, Richard J. Whitby, Malcolm H. Levitt
2020-05-13
Paper
DOI: 10.1039/D0CP01282C
Theoretical free energy profile and benchmarking of functionals for amino-thiourea organocatalyzed nitro-Michael addition reaction
2020-05-05
Paper
DOI: 10.1039/D0CP00481B
Excited-state proton transfer in protonated adrenaline revealed by cryogenic UV photodissociation spectroscopy
Jordan Dezalay, Michel Broquier, Satchin Soorkia
2020-04-28
Paper
DOI: 10.1039/D0CP01127D
Structural characterization of molybdenum–dinitrogen complex as key species toward ammonia formation by dispersive XAFS spectroscopy
Kazuya Arashiba, Shimpei Naniwa, Kazuo Kato, Hiromasa Tanaka, Kazunari Yoshizawa, Yoshiaki Nishibayashi
2020-04-23
Communication
DOI: 10.1039/C9CP06761B
Predicting the phase diagram of titanium dioxide with random search and pattern recognition
Aleks Reinhardt
2020-05-22
Paper
DOI: 10.1039/D0CP02513E
Radical⋯radical chalcogen bonds: CSD analysis and DFT calculations
Bartomeu Galmés, Jaume Adrover, Giancarlo Terraneo, Antonio Frontera, Giuseppe Resnati
2020-05-18
Paper
DOI: 10.1039/D0CP01643H
A computational exploration of the 1D TiS2(en) nanostructure for lithium ion batteries
Chun-Hao Huang, Elise Y. Li
2020-03-31
Paper
DOI: 10.1039/C9CP04675E
The effect of weighted averages when determining the speciation and structure–property relationships of europium(iii) dipicolinate complexes
Patrick R. Nawrocki, Nicolaj Kofod, Mikkel Juelsholt, Kirsten M. Ø. Jensen, Thomas Just Sørensen
2020-05-12
Paper
DOI: 10.1039/D0CP00989J
You might also like
Compound Q&A
What are the main uses of 4-Nitrophenyl phosphate disodium salt hexahydrate (CAS: 333338-18-4)?
4-Nitrophenyl phosphate disodium salt hexahydrate is primarily used as a substra...
333338-18-44-Nitrophenyl phosph...
Compound Q&A
What are the main uses of 2-(Trifluoromethyl)-1,3-oxazole-4-carboxylic Acid (CAS: 1060816-01-4)?
2-(Trifluoromethyl)-1,3-oxazole-4-carboxylic Acid (CAS: 1060816-01-4) is widely ...
1060816-01-42-(Trifluoromethyl)-...
Compound Q&A
How should 2-Fluoro-4-biphenylcarboxylic acid (CAS: 137045-30-8) be stored?
2-Fluoro-4-biphenylcarboxylic acid should be stored in a cool, dry place at room...
137045-30-82-Fluoro-4-biphenylc...
Compound Q&A
What industries use Prednisolone-21-Carboxylic Acid (CAS: 61549-70-0)?
Prednisolone-21-Carboxylic Acid is primarily used in the pharmaceutical industry...
61549-70-0Prednisolone-21-Carb...
Compound Q&A
How should 4-(Hydrazinomethyl)-1,2,3-benzenetriol (CAS: 3614-72-0) be stored?
4-(Hydrazinomethyl)-1,2,3-benzenetriol (CAS: 3614-72-0) should be stored in a co...
3614-72-04-(Hydrazinomethyl)-...
Compound Q&A
What industries use 4-Amino-1-methyl-1H-pyrazole-5-carboxylic acid hydrochloride (CAS: 92534-70-8)?
4-Amino-1-methyl-1H-pyrazole-5-carboxylic acid hydrochloride (CAS: 92534-70-8) i...
92534-70-84-Amino-1-methyl-1H-...
Compound Q&A
What regulatory guidelines apply to dehydropachymic acid (CAS: 77012-31-8)?
Dehydropachymic acid (CAS: 77012-31-8) is regulated by various agencies. It fall...
77012-31-8Dehydropachymic acid
Compound Q&A
What is the market or research trend for 6-[(2,2-Dimethylpropanoyl)amino]nicotinic acid (CAS: 898561-66-5)?
The market and research trends for 6-[(2,2-Dimethylpropanoyl)amino]nicotinic aci...
898561-66-56-[(2,2-Dimethylprop...
Compound Q&A
How should 1,10-Phenanthroline-2,9-dicarbaldehyde (CAS: 57709-62-3) be stored?
1,10-Phenanthroline-2,9-dicarbaldehyde should be stored in a cool, dry place awa...
57709-62-31,10-Phenanthroline-...
Compound Q&A
How is 5-Carbamoyl-11-oxo-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl acetate (CAS: 113952-21-9) typically synthesized?
5-Carbamoyl-11-oxo-10,11-dihydro-5H-dibenzo[b,f]azepin-10-yl acetate can be synt...
113952-21-95-Carbamoyl-11-oxo-1...
Source Journal
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
6-Bromo-3,4-dihydro-2H-1,4-benzoxazine hydrochloride (1:1)
CAS Number:
1260803-10-8
Molecular Formula:
C8H9BrClNO
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.