Equilibration d'imines cyclaniques

Richer, Jean–Claude; Perelman, David

doi:10.1139/v70-094

Cited by 16 publications

(3 citation statements)

References 3 publications

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“…2-Methyl-2-propynylcyclopentane-1,3-dione ( 1 ),11a N -cyclohexylidenecyclohexylamine, and 2-(2-propynyl)cyclohexanone ( 7 ) were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Oxygen-Directed Carbocyclizations of 2,3-Epoxy Alcohols: Stereoselective Construction of Polyfunctionalized Seven-Membered Rings by 7-Endo-Tet Ring Closures

et al. 1998

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The stereocontrolled construction of cycloheptanoid ring systems, relevant to sesquiterpenes and diterpenes of biological activity, is described. A new and highly efficient cyclization methodology provides stereocontrolled routes to polyfunctionalized and hydroxylated cycloheptanoid (and cyclohexanoid) rings. An alkyne or alkene terminus is shown to cyclize onto a 2,3-epoxy alcohol unit to give a cycloheptanoid ring incorporating syn-1,2-dihydroxylated functionality. Unusually, these carbocyclizations take place at the less substituted epoxide carbon atom of 2,3-epoxy alcohols, to the effective exclusion of alternative modes of cyclization. Chelation control is invoked to account for the highly efficient 7-endo-tet processes. Those processes occur at the expense of the normally more favored 6-exo-tet cyclizations. The little used Lewis acids SnBr4 and Sn(OTf)2 are shown to be effective in promoting acetylenic epoxy alcohol cyclizations. The effect of the relative configuration of the epoxy alcohol unit upon the outcome of the cyclization was studied.

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“…2-Methyl-2-propynylcyclopentane-1,3-dione ( 1 ),11a N -cyclohexylidenecyclohexylamine, and 2-(2-propynyl)cyclohexanone ( 7 ) were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Oxygen-Directed Carbocyclizations of 2,3-Epoxy Alcohols: Stereoselective Construction of Polyfunctionalized Seven-Membered Rings by 7-Endo-Tet Ring Closures

et al. 1998

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“…Important methods for the synthesis of primary amines include the alkylation of ammonia by organic halides and alcohols, [1][2][3] the reductive amination of carbonyl compounds, 4,5 the reduction of nitro compounds 6,7 and nitriles, 8,9 as well as other methods. [10][11][12] The synthesis of primary amines has been reported 13,14 from benzylamine and carbonyl compounds via the [1,3]-prototropic isomerisation of an imine followed by a hydrolysis step. This is a useful procedure for the preparation of primary amines avoiding the formation of secondary and tertiary amines as byproducts.…”

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confidence: 99%

Benzhydrylamine: An Effective Aminating Agent for the Synthesis of Primary Amines

Sun

Xing

Qin

et al. 2018

Journal of Chemical Research

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“…Diese beschrankt sich jedoch auf das N-Alkyliden-Teilgerust von 1. Die bekannte N-Alkyl-NAlkyliden-Isomerie der Verbindungen 1 13) 1aRt sich bei den Produkten 2 13C-NMRspektroskopisch (CH -N-Signale von z. B. l h / l i bzw.…”

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Borverbindungen, L Diethyl(substit.‐vinylamino)borane aus Triethylboran und N‐Alkylketiminen

1981

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Reines Triethylboran reagiert nur sehr langsam. Durch Zusatz von 0.5 -1 mol-% Diethyl(pivaloy1oxy)boran lafit sich die Ethan-Abspaltung jedoch deutlich beschleunigen, wobei die verschieden substituierten N-Alkylketimine unterschiedlich rasch reagieren (s. Tab. 1 und 7). In reinem Triethylboran entwickeln sich mit 1 mol N-Isopropyl(1-methylpropy1iden)amin (lb) in vier Tagen nur ca. 0.13 mol Ethan. Nach Zusatz von Diethyl(pivaloy1oxy)boran werden bereits in 24 h rnit 1 b sowie rnit N-Cyclohexylcyclododecylidenamin ( l h ) 0.85 mol Ethan frei. Die Cycloalkylidenderivate l c -g Liebigs Ann. Chem. 1981

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Equilibration d'imines cyclaniques

Abstract: not available

Cited by 16 publications

References 3 publications

Oxygen-Directed Carbocyclizations of 2,3-Epoxy Alcohols: Stereoselective Construction of Polyfunctionalized Seven-Membered Rings by 7-Endo-Tet Ring Closures

Oxygen-Directed Carbocyclizations of 2,3-Epoxy Alcohols: Stereoselective Construction of Polyfunctionalized Seven-Membered Rings by 7-Endo-Tet Ring Closures

Benzhydrylamine: An Effective Aminating Agent for the Synthesis of Primary Amines

Borverbindungen, L Diethyl(substit.‐vinylamino)borane aus Triethylboran und N‐Alkylketiminen

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