Nucleophilic addition and subsequent oxime-assisted ester hydrolysis of diethyl .beta.-ketopropylphosphonate

Livant, P.; Cocivera, Michael

doi:10.1021/jo00409a016

Cited by 4 publications

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“…Similarly, nucleophilic addition of hydroxylamine to the keto carbonyl group of diethyl -ketopropylphosphonate (29a) (R = OEt, R 1 = Me) in aqueous solution around pH = 7 leads to -oximo phosphonate 31a (Scheme 11) [13]. Using 1 H and 31 P NMR spectroscopy, during the reaction, it was possible to detect the carbinolamine 30a resulting from addition of hydroxylamine to the keto carbonyl group, the syn-and anti-isomers of the oxime of the diester 31a and the syn-and anti-isomers of the oxime of the monoester 32.…”

Section: Condensation Reactionmentioning

confidence: 99%

β-Hydroxyimino Phosphorus Derivatives. An Efficient Tool in Organic Synthesis

Santos¹,

Vicario²,

Alonso³

et al. 2011

COC

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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.

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Section: Condensation Reactionmentioning

confidence: 99%

β-Hydroxyimino Phosphorus Derivatives. An Efficient Tool in Organic Synthesis

Santos¹,

Vicario²,

Alonso³

et al. 2011

COC

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Phosphorus Derivatives of Hydroxylamines, Oximes and Hydroxamic Acids

Palácios

Santos

Vicario

et al. 2010

Patai's Chemistry of Functional Groups

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This comprehensive chapter, organized in three different sections, includes new topics focused on preparation and synthetic applications of phosphorus functionalized hydroxylamines, oximes and hydroxamic acids. The first section comprises the synthesis of phosphorus O ‐substituted hydroxylamines either through phosphorus‐oxygen or nitrogen‐oxygen single bond formation. The synthesis of N ‐substituted hydroxylamines is also covered in this first section by means of phosphorus‐nitrogen or carbon‐nitrogen bond formation reactions. This section also includes several transformations of phosphorus substituted hydroxylamines including among others: rearrangement, hydrolysis, reduction and oxidation reactions. Functionalized oximes containing phosphorus substituents including O ‐ and C ‐substituted oximes, and oximes with α‐ and β‐phosphorated moieties are covered in a second section. This provides an introduction to the common approaches to synthesize phosphorus substituted oximes, and the application of phosphorated oximes to the preparation of more elaborated compounds have been described. Some of the synthetic applications methods covered in the second section are fragmentation and rearrangement reactions, nucleophilic substitution at the phosphorus atom, intramolecular reactions, radical reactions, reduction of carbon‐nitrogen double bond, oxidation reactions, olefination reactions, dehydratation of oximes. The third section is dedicated to the synthesis and reactivity of phosphorus O ‐, N ‐, and C ‐substituted hydroxamic acid derivatives, spanning the few reports in the literature covering this topic. An extensive and current list of references and a subject index complete the chapter. Phosphorus Substituted Hydroxylamine Derivatives Phosphorus Substituted Oximes Phosphorus Substituted Hydroxamic Acid Derivatives Acknowledgments

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ChemInform Abstract: NUCLEOPHILIC ADDITION AND SUBSEQUENT OXIME‐ASSISTED ESTER HYDROLYSIS OF DIETHYL β‐KETOPROPYLPHOSPHONATE

Livant¹,

Cocivera²

1978

Chemischer Informationsdienst

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Nucleophilic addition and subsequent oxime-assisted ester hydrolysis of diethyl .beta.-ketopropylphosphonate

Cited by 4 publications

References 2 publications

β-Hydroxyimino Phosphorus Derivatives. An Efficient Tool in Organic Synthesis

β-Hydroxyimino Phosphorus Derivatives. An Efficient Tool in Organic Synthesis

Phosphorus Derivatives of Hydroxylamines, Oximes and Hydroxamic Acids

ChemInform Abstract: NUCLEOPHILIC ADDITION AND SUBSEQUENT OXIME‐ASSISTED ESTER HYDROLYSIS OF DIETHYL β‐KETOPROPYLPHOSPHONATE

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Nucleophilic addition and subsequent oxime-assisted ester hydrolysis of diethyl .beta.-ketopropylphosphonate

Cited by 4 publications

References 2 publications

&#946;-Hydroxyimino Phosphorus Derivatives. An Efficient Tool in Organic Synthesis

&#946;-Hydroxyimino Phosphorus Derivatives. An Efficient Tool in Organic Synthesis

Phosphorus Derivatives of Hydroxylamines, Oximes and Hydroxamic Acids

ChemInform Abstract: NUCLEOPHILIC ADDITION AND SUBSEQUENT OXIME‐ASSISTED ESTER HYDROLYSIS OF DIETHYL β‐KETOPROPYLPHOSPHONATE

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β-Hydroxyimino Phosphorus Derivatives. An Efficient Tool in Organic Synthesis

β-Hydroxyimino Phosphorus Derivatives. An Efficient Tool in Organic Synthesis