Tandem double acylation/[3,3]-rearrangement of aliphatic nitro compounds: a route to α-oxygenated oxime derivatives

Literature Information

Publication Date 2019-05-29
DOI 10.1039/C9OB01005J
Impact Factor 3.876
Authors

Yulia V. Nelyubina, Alexey Yu. Sukhorukov, Sema L. Ioffe, Andrey A. Tabolin


View Original

Abstract

A new tandem double acylation/rearrangement reaction of nitro compounds is described. It has a broad substrate scope allowing the mild and efficient synthesis of α-acyloxy oxime esters in high yields and regioselectivity. According to the obtained data, the mechanism for transformation was proposed. The utility of the obtained α-hydroxy oxime esters was demonstrated.

Related Literature

Solid-state NMR as a probe of anion binding: molecular dynamics and associations in a [5]polynorbornane bisurea host complexed with terephthalate

Aditya Rawal, James M. Hook, Ryan N. Robson, Daniel Gunzelmann, Frederick M. Pfeffer, Luke A. O'Dell

2015-07-28 Paper

DOI: 10.1039/C5CP03628C

Energy and temperature dependence of rigid unit modes in AlPO4-5

Gordon J. Kearley, Yun Liu, Dehong Yu, Richard A. Mole, Chris D. Ling, Ray L. Withers

2015-07-17 Paper

DOI: 10.1039/C5CP01723H

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

Impact of the plasmonic near- and far-field resonance-energy shift on the enhancement of infrared vibrational signals

Jochen Vogt, Christian Huck, Andrea Toma

2014-12-08 Paper

DOI: 10.1039/C4CP04851B

Strong electron donation induced differential nonradiative decay pathways for para and meta GFP chromophore analogues

Tanmay Chatterjee, Mrinal Mandal, Venkatesh Gude, Partha Pratim Bag, Prasun K. Mandal

2015-06-25 Paper

DOI: 10.1039/C5CP03086B

Soft X-ray absorption spectroscopy of Ar2 and ArNe dimers and small Ar clusters

Ghazal Jabbari, Tsveta Miteva, Vasili Stumpf, Kirill Gokhberg, Patrick O'Keeffe, Alessandra Ciavardini, Paola Bolognesi, Marcello Coreno, Lorenzo Avaldi, Elham Keshavarz, Maryam Ghandehari, Manijeh Tozihi, Carlo Callegari, Michele Alagia, Antti Kivimäki, Robert Richter

2015-07-22 Paper

DOI: 10.1039/C5CP03276H

Addition of low concentrations of an ionic liquid to a base oil reduces friction over multiple length scales: a combined nano- and macrotribology investigation

Hua Li, Anthony E. Somers, Patrick C. Howlett, Maria Forsyth, Rob Atkin

2016-02-05 Paper

DOI: 10.1039/C5CP07061A

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

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.