Radical cyclisation of α,ω-dinitroalkanes

Bowman, W. Russell; Jackson, Stuart W.

doi:10.1016/s0040-4020(01)89050-5

Cited by 26 publications

(1 citation statement)

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“…The free-radical substitution of the nitro group of the β-nitrostyrenes 1a − l to the alkenes 2a − p described herein is remarkable for the following reasons: (1) Usually the nitro group is a good activator for Michael addition and acts as a leaving group only in special cases . (2) Vinylic C−C coupling is usually carried out with sensitive organometallic reagents and halides and normally requires a catalyst such as Pd or Ni .…”

Section: Resultsmentioning

confidence: 99%

Free-Radical Reactions of Trialkylboranes with β-Nitrostyrenes To Generate Alkenes

1998

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beta-Nitrostyrenes 1 react with trialkylboranes under a nitrogen atmosphere to generate high yields of alkenes 2. The mechanism is proposed to be a free-radical reaction via NO(2)/alkyl substitution since the reaction is stimulated by the presence of a trace of oxygen in the nitrogen or tert-butyl peroxide or by photolysis and is retarded or inhibited by the addition of galvinoxyl to the solution.

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Section: Resultsmentioning

confidence: 99%

Free-Radical Reactions of Trialkylboranes with β-Nitrostyrenes To Generate Alkenes

1998

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Preparation of Difunctional Compounds

1995

Compendium of Organic Synthetic Methods

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Decarboxylative and Denitrative Trifluoromethylation for the Synthesis of C_vinylCF₃ Compounds with Togni (II) Reagent

et al. 2015

Adv Synth Catal

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Ah ighly efficient dimethylformamide (DMF)-promotedd ecarboxylativet rifluoromethylation of a,b-unsaturated carboxylic acids with Togni (II) reagent under metal-freec onditions has been developed. Ther eactions showed good yields,h igh stereoselectivitiesa nd excellent functional group tolerance.M echanistic studies confirmed that freeradical processes were involvedi nt his system since the CF 3 radical had been clearly trapped by scavengers.T his method has been extended to the denitrative trifluoromethylation of b-nitrostyrenes in the presence of an iron(III) catalyst.

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Radical cyclisation of α,ω-dinitroalkanes

Cited by 26 publications

References 26 publications

Free-Radical Reactions of Trialkylboranes with β-Nitrostyrenes To Generate Alkenes

Free-Radical Reactions of Trialkylboranes with β-Nitrostyrenes To Generate Alkenes

Preparation of Difunctional Compounds

Decarboxylative and Denitrative Trifluoromethylation for the Synthesis of C_vinylCF₃ Compounds with Togni (II) Reagent

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Radical cyclisation of α,ω-dinitroalkanes

Cited by 26 publications

References 26 publications

Free-Radical Reactions of Trialkylboranes with β-Nitrostyrenes To Generate Alkenes

Free-Radical Reactions of Trialkylboranes with β-Nitrostyrenes To Generate Alkenes

Preparation of Difunctional Compounds

Decarboxylative and Denitrative Trifluoromethylation for the Synthesis of CvinylCF3 Compounds with Togni (II) Reagent

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Product

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Decarboxylative and Denitrative Trifluoromethylation for the Synthesis of C_vinylCF₃ Compounds with Togni (II) Reagent