Methoxyamine Hydrochloride. An Improved Preparative Method.

Hjeds, Hans; Taub, William; Sinkkonen, Irma; Brunvoll, J.; Hinton, Merv

doi:10.3891/acta.chem.scand.19-1764

Cited by 29 publications

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“…A radioactive sample of methoxyamine hydrochloride was prepared on a small scale from [3H]-1973 dimethyl sulphate, NaNO2, Na2S205, acetic acid and ice according to the method developed by Hjeds (1965) but scaled down 100-fold. The product was recrystallized from ethanol; it did not reduce Fehling's solution, and hence was free of hydroxylamine.…”

Section: Methoxyaminementioning

confidence: 99%

Polypyrroles formed from porphobilinogen and amines by uroporphyrinogen synthetase of Rhodopseudomonas spheroides

Davies

Neuberger

1973

Biochemical Journal

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1. Uroporphyrinogen I synthetase of Rhodopseudomonas spheroides was purified more than 200-fold from the soluble protein of broken bacterial cells. The enzyme had molecular weight 36000, an isoelectric point of 4.46 and migrated as a single active protein band on disc-gel electrophoresis at pH7.5 and 8.9. 2. The enzyme consumed porphobilinogen and formed uroporphyrinogen at pH8.2 without the accumulation of intermediates. In the presence of hydroxylamine, ammonia or methoxyamine the production of porphyrinogen was inhibited and the enzyme formed open-chain polypyrroles instead. 3. These polypyrroles behaved like uroporphyrinogen on Sephadex G-25; they were colourless and had unsubstituted alpha-pyrrolic positions. The inhibitory amines were incorporated into the molecules. 4. The polypyrroles formed porphyrins non-enzymically and the cyclization reaction was accompanied by the release of the inhibitory amine. Exchange of the amino function of the original porphobilinogen in the polypyrrole was complete with hydroxylamine and almost complete with methoxyamine, both ammonia and methoxyamine being present in the polypyrrolic material. 5. The behaviour, properties and composition of the radioactive hydroxylamine derivative were consistent with a tetrapyrrolic structure, probably a pyrrylmethane, that was not cyclized, rather than with di-, tri- or penta-pyrrolic structures. No monopyrrolic or dipyrrolic Ehrlich-positive material was released on cyclization. The ammonia and methoxyamine derivatives had properties similar to the hydroxylamine derivative. 6. Another modified pyrrole was detected only in experiments with hydroxylamine. It differed from both porphobilinogen and known dipyrroles and appeared to be a monopyrrole. 7. The participation of positively charged reaction centres in the enzymic mechanism, particularly in the cyclization step, is discussed.

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Section: Methoxyaminementioning

confidence: 99%

Polypyrroles formed from porphobilinogen and amines by uroporphyrinogen synthetase of Rhodopseudomonas spheroides

Davies

Neuberger

1973

Biochemical Journal

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“…Acetone O ‐(2,4,6‐trimethylphenylsulfonyl)oxime36 1 , acetone oxime O ‐tosylate37 2 and O ‐methylhydroxylamine38 3 were prepared and purified according to the methods described in the literature.…”

Section: Methodsmentioning

confidence: 99%

Cosolvent‐promoted electrophilic amination of organozinc reagents

Daşkapan¹,

Yeşilbağ²,

Koca³

2009

Applied Organom Chemis

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“…43,44 O-Methylhydroxylamine was prepared and purified by the method of Hjeds. 52 The general procedure for the competitive amination of a substituted phenylmetal with phenylmetal was as follows. Into a flame-dried, two-necked, round-bottomed flask equipped with a stirring bar and kept at À15 C, a substituted phenylmagnesium bromide (16b-g) (20 mmol) and phenylmagnesium bromide (16a) (20 mmol) were placed with syringes.…”

Section: Methodsmentioning

confidence: 99%

Kinetic study of the amination of Grignard reagents and cuprates with O‐methylhydroxylamine

Erdık

Eroğlu

Kâhya

2005

J of Physical Organic Chem

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Substituent effects on the rate of electrophilic amination of phenylmagnesium bromides, magnesium diphenylcuprates and catalytic phenylzinc cyanocuprates with O‐methyhydroxylamine in THF were investigated in a competitive kinetic study. Rate data and Hammett substituent constants are discussed on the basis of proposed mechanisms for the substitution reactions of these organometallics with an electrophilic amino transfer reagent. Copyright © 2005 John Wiley & Sons, Ltd.

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Methoxyamine Hydrochloride. An Improved Preparative Method.

Cited by 29 publications

References 0 publications

Polypyrroles formed from porphobilinogen and amines by uroporphyrinogen synthetase of Rhodopseudomonas spheroides

Polypyrroles formed from porphobilinogen and amines by uroporphyrinogen synthetase of Rhodopseudomonas spheroides

Cosolvent‐promoted electrophilic amination of organozinc reagents

Kinetic study of the amination of Grignard reagents and cuprates with O‐methylhydroxylamine

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