Abstract
The purpose of this review article is to illustrate synthetic aspects of functionalized phosphorus derivatives containing an oximo moiety at the beta-position. First section will be focused on the synthesis of phosphine oxides, phosphonates or phosphonium salts containing an oxime group. The synthesis of these derivatives comprises the carbon – phosphorus single bond construction by reaction of haloximes with phosphorus derivatives, nucleophilic addition of phosphorus reagents to carbonyl compounds, or nucleophilic addition of phosphorus reagents to nitro olefins. This section will also concentrate on the most practical routes for the synthesis of the target compounds, through carbon – nitrogen double bond formation, which are as follows: condensation processes of carbonyl compounds and hydroxylamine derivatives or addition of hydroxylamines to allenes or alkynes. The preparative use of beta-oximo phosphorus derivatives as synthetic intermediates will be discussed in a second section, comprising olefination reaction, oxidation of oximes to nitrile oxides by reaction at the C-N double bond of the oxime moiety, oxidation of these substrates to nitrosoalkenes, reduction to the corresponding hydroxylamines and some reactions at the hydroxyl group of the hydroxyimino moiety.
Keywords: β-Hydroxyimino phosphorus derivatives, α-haloximes, nitro olefins, nitrile oxides, nitrosoalkenes, Condensation Reaction, Olefination Reaction, Oxime Reductions, Nitrosoalkene Formation, Cyclization Reactions, Dehydratation of Oximes, O-Functionalization Reactions, diphenyl phosphine oxide (HPOPh2), fluoroalkyl p-toluenesulfonyl ketoximes, Grignard reagents
Current Organic Chemistry
Title: β-Hydroxyimino Phosphorus Derivatives. An Efficient Tool in Organic Synthesis
Volume: 15 Issue: 10
Author(s): Jesus M. de los Santos, Javier Vicario, Concepcion Alonso and Francisco Palacios
Affiliation:
Keywords: β-Hydroxyimino phosphorus derivatives, α-haloximes, nitro olefins, nitrile oxides, nitrosoalkenes, Condensation Reaction, Olefination Reaction, Oxime Reductions, Nitrosoalkene Formation, Cyclization Reactions, Dehydratation of Oximes, O-Functionalization Reactions, diphenyl phosphine oxide (HPOPh2), fluoroalkyl p-toluenesulfonyl ketoximes, Grignard reagents
Abstract: The purpose of this review article is to illustrate synthetic aspects of functionalized phosphorus derivatives containing an oximo moiety at the beta-position. First section will be focused on the synthesis of phosphine oxides, phosphonates or phosphonium salts containing an oxime group. The synthesis of these derivatives comprises the carbon – phosphorus single bond construction by reaction of haloximes with phosphorus derivatives, nucleophilic addition of phosphorus reagents to carbonyl compounds, or nucleophilic addition of phosphorus reagents to nitro olefins. This section will also concentrate on the most practical routes for the synthesis of the target compounds, through carbon – nitrogen double bond formation, which are as follows: condensation processes of carbonyl compounds and hydroxylamine derivatives or addition of hydroxylamines to allenes or alkynes. The preparative use of beta-oximo phosphorus derivatives as synthetic intermediates will be discussed in a second section, comprising olefination reaction, oxidation of oximes to nitrile oxides by reaction at the C-N double bond of the oxime moiety, oxidation of these substrates to nitrosoalkenes, reduction to the corresponding hydroxylamines and some reactions at the hydroxyl group of the hydroxyimino moiety.
Export Options
About this article
Cite this article as:
M. de los Santos Jesus, Vicario Javier, Alonso Concepcion and Palacios Francisco, β-Hydroxyimino Phosphorus Derivatives. An Efficient Tool in Organic Synthesis, Current Organic Chemistry 2011; 15 (10) . https://dx.doi.org/10.2174/138527211795378146
DOI https://dx.doi.org/10.2174/138527211795378146 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |

- Author Guidelines
- Bentham Author Support Services (BASS)
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
Aripiprazole-Induced Pathological Gambling: A Report of 3 Cases
Current Drug Safety Targeting Signaling Pathways in Multiple Myeloma
Current Pharmaceutical Biotechnology The Role of Aryl Hydrocarbon Receptor-Regulated Cytochrome P450 Enzymes in Glioma
Current Pharmaceutical Design Small Molecules Antileishmanials: A Review
Letters in Drug Design & Discovery Population Based Helicobacter pylori Screening and Eradication: Advances Versus Side Effects
Current Pharmaceutical Design Adult and Embryonic Stem Cells in Cartilage Repair
Current Rheumatology Reviews Application of Bone Marrow Stem Cell Based Therapy in Bone Loss Diseases
Current Pharmaceutical Design Effects of Lipid-Lowering Agents on Inflammation, Haemostasis and Blood Pressure
Current Pharmaceutical Design Marine Peptides and Related Compounds in Clinical Trial+
Anti-Cancer Agents in Medicinal Chemistry Parkinson’s Disease: Is there a Role for Dietary and Herbal Supplements?
CNS & Neurological Disorders - Drug Targets Insulin Resistance and Diabetes in HIV Infection
Recent Patents on Anti-Infective Drug Discovery Leptin, Estrogens and Cancer
Mini-Reviews in Medicinal Chemistry PDE4D Gene in the STRK1 Region on 5q12: Susceptibility Gene for Ischemic Stroke
Current Medicinal Chemistry Potential Anti-Catabolic and Anabolic Properties of Strontium Ranelate
Current Molecular Pharmacology Signaling Pathways Associated with Inflammatory Bowel Disease
Recent Patents on Inflammation & Allergy Drug Discovery Biology of Cox-2: An Application in Cancer Therapeutics
Current Drug Targets Studies on the Pathophysiology and Genetic Basis of Migraine
Current Genomics Current Advances in the Treatment of Parkinsons Disease with Stem Cells
Current Neurovascular Research Investigating Drug Repositioning Approach to Design Novel Prodrugs for Colon-specific Release of Fexofenadine for Ulcerative Colitis
Current Drug Delivery Minocycline as Add-On Treatment Decreases the Negative Symptoms of Schizophrenia; A Randomized Placebo-Controlled Clinical Trial
Recent Patents on Inflammation & Allergy Drug Discovery