Reactions of 1-Halo-1-nitroso- and 1-Halo-1-nitrocycloalkanes with Triphenylphosphine. A New Synthesis of Lactam

Sakai, Ikuo; Kawabe, Norio; Ohno, Masaji

doi:10.1246/bcsj.52.3381

Cited by 28 publications

(7 citation statements)

References 6 publications

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“…rather than metathetic exchange and/or direct oxidation [21] of 11 (vide infra). Such behaviour clearly points to the nitroso ester 11 as the likely cleavage partner in the oxida-tion.…”

mentioning

confidence: 99%

Oxidation of Benzylic Alcohols and Ethers to Carbonyl Derivatives by Nitric Acid in Dichloromethane

Strazzolini

Runcio

2003

Eur J Org Chem

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Nitric acid in dichloromethane may be successfully employed for the oxidation of benzylic alcohols and ethers to the corresponding carbonyl compounds. The proposed method proved to be of general applicability, affording very good yields of aldehydes and ketones and showing interesting chemoselectivity in many instances, allowing competitive aromatic nitration to be avoided, as well as − in the case of aldehydes − any further oxidation to carboxylic acids. The reaction probably proceeds by a radical mechanism, the active species in the oxidation process being NO2. Competitive formation of nitro esters was observed in some cases, whereas poor results were obtained with allylic and non‐benzylic substrates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…rather than metathetic exchange and/or direct oxidation [21] of 11 (vide infra). Such behaviour clearly points to the nitroso ester 11 as the likely cleavage partner in the oxida-tion.…”

mentioning

confidence: 99%

Oxidation of Benzylic Alcohols and Ethers to Carbonyl Derivatives by Nitric Acid in Dichloromethane

Strazzolini

Runcio

2003

Eur J Org Chem

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“…81,82 If necessary, storage over CaCl 2 at −8°C in a brown glass bottle is recommended. Careful neutralization of tBuOCl over thioanisole 83 and of 1a,b over triphenylphosphine 84 is strongly advised before disposal.…”

Section: Typical Runs Cautionmentioning

confidence: 99%

A modular, low footprint and scalable flow platform for the expedient α-aminohydroxylation of enolizable ketones

et al. 2021

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“…Such a mechanism finds direct precedence in a similar ring expansion during the reaction of 1-chloro-1-nitrosocyclohexane during its reaction with triphenyl phosphine. 28 …”

Section: Phopshine-mediated Beckmann Rearrangementmentioning

confidence: 99%

Ring expansions of acyloxy nitroso compounds

Hadimani

Mukherjee

Banerjee

et al. 2015

Tetrahedron Letters

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Treatment of cyclopentanone and cyclobutanone-derived oximes with lead (IV) tetraacetate gives the bright blue acyloxy nitroso compounds, which upon basic hydrolysis yields the ring expansion product cyclic hydroxamic acids in 12–81% yield. Reactions of substituted cyclopentanones provide ring expanded products where the –NOH group regioselectively inserts to the more substituted position and gives a better yield compared to the treatment of the same ketone with a basic solution of Piloty’s acid. Reaction of phosphines with acyloxy nitroso compounds generally generates a ring-expanded Beckmann rearrangement product that can be hydrolyzed to the corresponding lactam. Acyloxy nitroso compounds that undergo rapid hydrolysis to HNO do not show this ring expansion reactivity. These results further demonstrate the versatility of acyloxy nitroso compound to yield structurally complex materials.

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Reactions of 1-Halo-1-nitroso- and 1-Halo-1-nitrocycloalkanes with Triphenylphosphine. A New Synthesis of Lactam

Cited by 28 publications

References 6 publications

Oxidation of Benzylic Alcohols and Ethers to Carbonyl Derivatives by Nitric Acid in Dichloromethane

Oxidation of Benzylic Alcohols and Ethers to Carbonyl Derivatives by Nitric Acid in Dichloromethane

A modular, low footprint and scalable flow platform for the expedient α-aminohydroxylation of enolizable ketones

Ring expansions of acyloxy nitroso compounds

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