The synthesis of functionalized tetrasubstituted olefins. Calcium amalgam - a novel reducing agent

Kornblum, Nathan; Cheng, Leung

doi:10.1021/jo00437a042

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Cited by 17 publications

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“…This type of bond formation is usually not easily achieved using any other reactions in organic synthesis. The adducts from an aliphatic S RN 1 reaction are regarded as precursors for further palladium coupling materials [16] or tri- or tetrasubstituted alkenes [17,18,19,20,21,22].…”

Section: Introductionmentioning

confidence: 99%

Preparation of SRN1-Type Coupling Adducts from Aliphatic gem-Dinitro Compounds in Ionic Liquids

Kamimura

Toyoshima

2012

Molecules

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S RN 1-type coupling adducts are readily prepared by the reaction between -sulfonylesters or -cyanosulfones and gem-dinitro compounds in ionic liquids. The reactions progress smoothly and recovered ionic liquids can be used for several iterations, as long as they are washed with water to remove alkali metallic salts. The reaction rate is slower than the corresponding S RN 1 reaction in DMSO, but no acceleration on irradiation or no inhibition in the presence of m-DNB are observed.

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