One-Pot Transformation of Alkyl Bromides into Primary Amines via the Staudinger Reaction

Koziara, A.; Osowska-Pacewicka, Krystyna; Zawadzki, S.; Zwierzak, A.

doi:10.1055/s-1985-31155

Cited by 56 publications

(23 citation statements)

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“…40 Nucleophilic displacement of the bromide from the bromo-alkene with azide afforded intermediate 3, which was easily converted to the primary amine 4 using the Staudinger reduction. 41 The coupling reaction between the acid 2 and amine 4 derivatives to generate the amido compound 5 was performed by using the carbodiimide chemistry to activate the carboxylic acid group into an active ester. 42 Then, the acetyl group of compound 5 was deprotected using K 2 CO 3 in methanol to obtain the compound 6 in high yield (70%).…”

Section: Synthesis Of Amido and Ureido Silylated Coupling Agentsmentioning

confidence: 99%

Epoxy-Terminated Self-Assembled Monolayers Containing Internal Urea or Amide Groups

et al. 2015

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We report the synthesis of new coupling agents with internal amide or urea groups possessing an epoxy-terminal group and trimethoxysilyl-anchoring group. The structural characterizations of the corresponding self-assembled monolayers (SAMs) were performed by polarization modulation infrared reflection adsorption spectroscopy (PM-IRRAS). The molecular assembly is mainly based on the intermolecular hydrogen-bonding between adjacent amide or urea groups in the monolayers. Because of the steric hindrance of amide or urea groups, the distance between the alkyl chains is too large to establish van der Waals interactions, inducing their disorder. The reactivity of the epoxy-terminal groups was successfully investigated through reaction with a fluorescent probe. We show that SAMs containing internal urea or amide groups exhibited a higher density of accessible epoxide groups than the corresponding long-chain (C22) glycidyl-terminated SAM.

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Section: Synthesis Of Amido and Ureido Silylated Coupling Agentsmentioning

confidence: 99%

Epoxy-Terminated Self-Assembled Monolayers Containing Internal Urea or Amide Groups

et al. 2015

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“…Again, other methods should ultimately be investigated (e.g., azide opening of an epoxide) but for now we preferred to retain the C-C double bond as a site that could be further modified. The allylic bromide was readily prepared with NBS and was then converted to the azide with NaN 3 (23). We sought to avoid isolation and purification of this potentially dangerous intermediate, so it was used in a one-pot procedure (24) by reaction with PPh 3 (the Staudinger reaction), then water to hydrolyze the iminophosphorane, and finally a reagent for introducing a protecting group to the newly generated free amine.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of polyfunctional fatty amines from sophorolipid‐derived 17‐hydroxy oleic acid

Zerkowski

Solaiman

2006

J Americ Oil Chem Soc

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A series of mono-and diamines and one triamine have been prepared using methyl 17-hydroxy oleate as the common starting material. The 17-hydroxy oleate is an abundant bioderived material obtained from acid alcoholysis of sophorolipids, which in turn are produced by fermentation of agricultural by-products. Incorporation of the amino unit(s) can be selectively performed at either end of the chain or at its middle. The chief synthetic reactions used are allylic bromination, Curtius rearrangement, and the Mitsunobu reaction. These fatty amines also possess functionality such as hydroxy groups, carboxylic acids, and C-C double bonds. The amines are isolated in protected form using a variety of protecting groups, the identities of which can be selected on the basis of the intended use of the amine. These novel compounds will be of interest in the preparation of highly functionalized polymers and surfactants, among other areas.FIG. 1. The 17-hydroxy oleic acid that is the precursor for new compounds discussed in this work is obtained from acid alcoholysis of sophorolipids, which are predominantly acetylated macrolactones. Molecule 1 can be derivatized at its carboxyl, olefin, or hydroxy group. 622

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“…1 H, 13 C and 31 P NMR spectra were recorded on a Bruker ARX400 spectrometer. The following compounds were prepared, according to general reported procedures: chlorodioxaphospholane, [27] dichlorodiethylphosphoramidite, [28] diethylphosphoroamidous dichloride, [29] benzylazide, [30] octylazide, [30] 4-nitrobenzylazide, [30] 4-methylphenylazide, [31] phenylazide, [31] tosylazide. [32] (2R)-1-N-Phenylamino-2-propanol: Prepared from (R)-propylene oxide, following general reported procedure; [33] [a] 20 D À 16.…”

Section: Methodsmentioning

confidence: 99%

Imide–Amide Rearrangement of Cyclic Phosphorimidates: A Mechanistic Study

2001

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Studies aimed at the development of new synthetic pathways for the preparation of chiral cyclic oxaza and diaza phosphoramides suitable for use in asymmetric chemistry led us to the investigation of the imide ± amide rearrangement of cyclic phosphorimidates. As a result of this work new types of oligomeric organophosphorus compounds, formed by a novel 1,4-addition type ring opening polymerisation, were identified. These compounds are the stable intermediates of the imide ± amide rearrangement, which upon heating yield the previously reported rearranged product. A detailed study of the mechanism of the Lewis acid catalysed imide ± amide rearrangement and stereochemical control of the final products is reported. As a result, the full mechanism was elucidated and evidence of retention of configuration at the rearranged carbon atom is presented. Substituent effects were rationalised based on molecular modelling calculations.

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One-Pot Transformation of Alkyl Bromides into Primary Amines via the Staudinger Reaction

Cited by 56 publications

References 0 publications

Epoxy-Terminated Self-Assembled Monolayers Containing Internal Urea or Amide Groups

Epoxy-Terminated Self-Assembled Monolayers Containing Internal Urea or Amide Groups

Synthesis of polyfunctional fatty amines from sophorolipid‐derived 17‐hydroxy oleic acid

Imide–Amide Rearrangement of Cyclic Phosphorimidates: A Mechanistic Study

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