Synthesis of 1-halo-N,N-bis(silyloxy)enamines

Kunetsky, Roman A.; Dilman, Alexander D.; Стручкова, Марина И.; Belyakov, Pavel A.; Korlyukov, Alexander A.; Ioffe, Sema L.; Tartakovsky, Vladimir A.

doi:10.1016/j.mencom.2007.03.019

Cited by 6 publications

(3 citation statements)

References 15 publications

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“…Synthetic routes to cyclic oxime ethers, particularly from bis(oxy)enamines (which are typically prepared from nitro compounds; , Scheme , c and f) were comprehensively reviewed in 2011; below, we focus on reactions leading to the acyclic oxime species. These reactions are typically promoted by the R 3 Si + species, − or they proceed even in the absence of a promoter, and lead to oxime ethers XCR 1 R 2 C(R 3 )NOE (g) functionalized at the α-position or to appropriate oximes (X = amino, , azido, , hetaryl, oxy, , chloride; Scheme ).…”

Section: Metal-mediated Generation Of Oximesmentioning

confidence: 99%

Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

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This review classifies and summarizes the past 10-15 years of advancements in the field of metal-involving (i.e., metal-mediated and metal-catalyzed) reactions of oximes. These reactions are diverse in nature and have been employed for syntheses of oxime-based metal complexes and cage-compounds, oxime functionalizations, and the preparation of new classes of organic species, in particular, a wide variety of heterocyclic systems spanning small 3-membered ring systems to macroheterocycles. This consideration gives a general outlook of reaction routes, mechanisms, and driving forces and underlines the potential of metal-involving conversions of oxime species for application in various fields of chemistry and draws attention to the emerging putative targets.

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Section: Metal-mediated Generation Of Oximesmentioning

confidence: 99%

Metal-Involving Synthesis and Reactions of Oximes

et al. 2017

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“…Nitromethane (nitroalkane) also had a dual role, that is, as the solvent and as the substrate. In view of this, the suggested pathway for the reaction (C–S bond formation) is through the formation of a silyl nitronate (Scheme ) , , …”

Section: Resultsmentioning

confidence: 99%

Highly Efficient One‐Step Synthesis of N‐Trimethylsiloxy Alkyl Imidothioates

Kuciński

Hreczycho

2016

Eur J Org Chem

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A hitherto unknown synthetic pathway for the synthesis of N‐trimethylsiloxy alkyl imidothioates has been presented. The catalyst‐free route uses a range of aromatic, aliphatic, and heterocyclic thiols in the presence of nitroalkanes and hexamethyldisilazane (HMDS). This unusual method expands upon the knowledge of nitro compounds and demonstrates their importance not only as solvents but also as valuable organic reagents. This reaction proceeds under mild conditions and is characterized by excellent yields and a facile workup.

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“…2 The presence of two electronegative groups bonded to the same carbon atom exerts influence not only on its CH-acidity but also on the reactivity of both substituents. Nitro groups in gem-halo-nitro compounds can be easily silylated giving N,N-bis(silyloxy)enamines 3 -products that attract considerable interest owing to their synthetic applications -whereas the halogen atoms can undergo various substitution reactions. 4 The synthetic potential of gem-chloro-nitrocarboxylic acids comes from their polyfunctional nature.…”

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confidence: 99%

Titanium(IV) Enolates of 2-Nitrocarboxylic Esters and Their Oxidative Chlorination. A Convenient Route to α-Chloro-α-nitrocarboxylates

Cież¹,

Kalinowska‐Tłuścik²

2012

Synlett

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A new method for the synthesis of 2-chloro-2-nitrocarboxylic esters from 2-nitrocarboxylates is described. The procedure consists of the oxidative chlorination of titanium(IV) enolates of 2nitro esters in the presence of ammonium nitrate. Esters of 2-chloro-2-nitrocarboxylic acids are formed in very good to quantitative yields. Application of this method for the chlorination of a,a¢-dinitrodicarboxylates leads to a,a¢-dichloro-a,a¢-dinitrocarboxylic esters with high meso-diastereoselectivity. The absence of ammonium nitrate from the reaction mixture affects the reduction of nitro groups and leads to partial transformation of 2-nitrocarboxylic esters into 2-(hydroxyimino)carboxylates.

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Synthesis of 1-halo-N,N-bis(silyloxy)enamines

Cited by 6 publications

References 15 publications

Metal-Involving Synthesis and Reactions of Oximes

Metal-Involving Synthesis and Reactions of Oximes

Highly Efficient One‐Step Synthesis of N‐Trimethylsiloxy Alkyl Imidothioates

Titanium(IV) Enolates of 2-Nitrocarboxylic Esters and Their Oxidative Chlorination. A Convenient Route to α-Chloro-α-nitrocarboxylates

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