Synthesis of Oximes and Hydroxamic Acids

Porcheddu, Andrea; Giacomelli, Giampaolo

doi:10.1002/9780470682531.pat0458

Cited by 7 publications

(6 citation statements)

References 201 publications

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“…These classical syntheses of hydroxamic acids are highly dependent on the structure of the target molecules and product isolation is often extremely difficult 9…”

Section: Methodsmentioning

confidence: 99%

One‐Pot Synthesis of Hydroxamic Acids from Aldehydes and Hydroxylamine

Dettori¹,

Gaspa²,

Porcheddu³

et al. 2014

Adv Synth Catal

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“…These classical syntheses of hydroxamic acids are highly dependent on the structure of the target molecules and product isolation is often extremely difficult 9…”

Section: Methodsmentioning

confidence: 99%

One‐Pot Synthesis of Hydroxamic Acids from Aldehydes and Hydroxylamine

Dettori¹,

Gaspa²,

Porcheddu³

et al. 2014

Adv Synth Catal

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“…Moreover, the peak at wavenumber of 1560 cm −1 , assigned to NH bending of amide, can be observed in the spectrum of the hydroxylamine‐treated PC. This finding indicates that hydroxylamine decomposed fatty acid ester of PC and then liberated free fatty acids in the form of fatty hydroxamic acid (RCONHOH), which is known as the product of the cleavage of esters with hydroxylamine . The cleavage of fatty acid ester of PC with hydroxylamine is demonstrated in Figure .…”

Section: Resultsmentioning

confidence: 86%

“…This finding indicates that hydroxylamine decomposed fatty acid ester of PC and then liberated free fatty acids in the form of fatty hydroxamic acid (RACOANHOH), which is known as the product of the cleavage of esters with hydroxylamine. 25,26 The cleavage of fatty acid ester of PC with hydroxylamine is demonstrated in Figure 4. Hydroxylamine completely cleaves the ester linkages of PC at C1 and C2 position to give fatty hydroxamic acid and glycerophosphocoline, which is a water soluble compound.…”

Section: Resultsmentioning

confidence: 99%

Molecular structure and storage hardening of natural rubber: Insight into the reactions between hydroxylamine and phospholipids linked to natural rubber molecule

Nimpaiboon

Sriring

Sakdapipanich

2016

J of Applied Polymer Sci

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The effect of hydroxylamine on the molecular structure and storage hardening of natural rubber (NR) was investigated by the treatment of deproteinized NR (DPNR) latex with hydroxylamine. The hydroxylamine treatment decreased the content of long‐chain fatty acid ester groups in DPNR from about 2–0.7 mol per rubber molecule. The molecular weight and molecular weight distribution changed apparently after treatment with hydroxylamine. The relative intensity of the 1H NMR signals corresponding to phospholipids at the α‐terminal group decreased after the hydroxylamine treatment. The Huggins ‘k’ constant of hydroxylamine‐treated DPNR showed the liberation of linear rubber molecules caused by decomposition of branch points derived from phospholipids. The absence of storage hardening in hydroxylamine‐treated DPNR was observed to be caused by not only the reaction of hydroxylamine and aldehyde groups but also the removal of phospholipids as well as the breakdown of phospholipid aggregations as a result of hydroxylamime, contributing to the establishment of a newly proposed mechanism of hydroxylamine on the inhibition of storage hardening in NR. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 43753.

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“…Enantiopure ( R )-2′-methylbutyrophenone ( 1 R ) was prepared by Enders’ asymmetric alkylation of propiophenone with iodomethane , (Scheme c). Unlike aldoximes, no general methods to prepare stereochemically pure ketoximes exist . The only separation technique found in the literature includes a multistep recrystallization of diastereomeric mixture leading to a large loss of oxime .…”

Section: Results and Discussionmentioning

confidence: 99%

Stereocontrol in Preparation of Cyclopalladated Alkylaromatic Oximes and Evaluation of Their Stereoselective Esterase-Type Catalytic Activity

et al. 2017

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The stereochemistry of 2′-methylbutyrophenone oxime, the rates of ortho-palladation of its E-and Zisomers, and catalytic activity of the respective Pd complexes were studied. The full stereoisomeric composition of oximes was established for the first time by means of supercritical fluid chromatography on chiral polysaccharide column. It was shown that enantiomeric excesses of both E/Z-isomers of (S)-2′-methylbutyrophenone oxime (1S) and (R)-2′-methylbutyrophenone oxime (1R) were equal to 92 ± 2. The cyclopalladation study revealed that while E-isomer is orthopalladated very quickly its Z-counterpart does not enter this reaction. However, upon coordination to Pd(II), Z-oxime slowly isomerizes into E-form with fast subsequent cyclopalladation, so it was possible to perform ortho-palladation of E-oxime in kinetic resolution mode with removal of unreacted Zoxime. Comparatively rare cis-structure of cyclopalladated oxime dimer was proved by means of single-crystal X-ray study. For the first time, it was shown that ortho-palladated chiral oximes behave as enantioselective catalyst in the hydrolysis of chiral esters.

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Synthesis of Oximes and Hydroxamic Acids

Abstract: Synthesis of Oximes Synthesis of Hydroxamic Acids

Cited by 7 publications

References 201 publications

One‐Pot Synthesis of Hydroxamic Acids from Aldehydes and Hydroxylamine

One‐Pot Synthesis of Hydroxamic Acids from Aldehydes and Hydroxylamine

Molecular structure and storage hardening of natural rubber: Insight into the reactions between hydroxylamine and phospholipids linked to natural rubber molecule

Stereocontrol in Preparation of Cyclopalladated Alkylaromatic Oximes and Evaluation of Their Stereoselective Esterase-Type Catalytic Activity

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