Regeneration of Carbonyl Compounds from the Corresponding Oximes

Corsaro, Antonino; Chiacchio, Ugo; Pistarà, Venerando

doi:10.1055/s-2001-17700

Cited by 73 publications

(28 citation statements)

References 124 publications

(134 reference statements)

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“…Therefore, the usefulness of nitrosoalkenes [48] as conjugate addition acceptors [49], coupled with the easy conversion of the nitroso group into other functionalities, such as oximes and ketones [50], or their ability to act as dienes in hetero-Diels-Alder reactions for the preparation of 1,2-oxazine derivatives [51], have been reported. The synthesis of nitrosoalkenes containing a phosphorus substituent at C 4 has been scarcely explored.…”

Section: Nitrosoalkene Formationmentioning

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: Nitrosoalkene Formationmentioning

confidence: 99%

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

Santos¹,

Vicario²,

Alonso³

et al. 2011

COC

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“…OH Me NH MeO NH 2 OMe HCl buffer (10) S N 1 substitutions also proceed easily in compounds forming highly stabilized secondary carbocations such as benzyhydrol 49 , ferrocene 50 and analogous systems 51 . A variety of leaving groups can be utilized in these reactions including halides, alkoxy and alkylthio in the presence of mercury salts and ethers.…”

Section: Mementioning

confidence: 99%

Synthesis of Hydroxylamines

Melman

2010

Patai's Chemistry of Functional Groups

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Introduction Hydroxylamines through Hydrolysis of Hydroxamic Acids, Oximes and Nitrones Synthesis of Hydroxylamines through Alkylation and Arylation of other Hydroxylamines Hydroxylamines through Reduction Reactions Hydroxylamines through Addition to the C  N Double Bond of Oximes, Oxime Ethers and Nitrones Hydroxylamines through Addition to the N  O Double Bond of Nitroso and Nitro Compounds Hydroxylamines through Oxidation of Amines Hydroxylamines through Cycloaddition Reactions

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“…Recently the problem of regeneration of aldehydes from oximes from available methods has been extensively reviewed. [17] Although some of these methods are carried out under mild reaction conditions, most of them require strong acidic media, a strong oxidizing agent, rare or poisonous reagents, or sometimes long reaction times. Thus there is still a need to develop a new and facile procedure for the regeneration of carbonyl compounds from oximes.…”

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confidence: 99%