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1989•Journal of the Chemical Society Chemical CommunicationsRequires access

Effect of the phosphonate group on the reactivity of carbenes. Neighbouring phosphonate group participation

Hideo Tomioka, Katsuyuki Hirai

Open publisher page 14 citations

Abstract

The electrophilicity of phosphonylcarbenes is dramatically reduced as one changes the neighbouring group from the phosphonate ester to the acid anion, and phosphonate carbenes are experimentally classified as typical nucleophiles; the results are nicely explained in terms of neighbouring phosphonate group participation in which the vacant p orbital strongly interacts with the phosphonate oxygen anion resulting in suppression of the availability of the vacant p orbital.

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What this paper is about

The electrophilicity of phosphonylcarbenes is dramatically reduced as one changes the neighbouring group from the phosphonate ester to the acid anion, and phosphonate carbenes are experimentally classified as typical nucleophiles; the results are nicely explained in terms of neighbouring phosphonate group participation in which the vacant p orbital strongly interacts with the phosphonate oxygen anion resulting in suppression of the availability of the vacant p orbital.

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OpenAlex reports 14 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

The electrophilicity of phosphonylcarbenes is dramatically reduced as one changes the neighbouring group from the phosphonate ester to the acid anion, and phosphonate carbenes are experimentally classified as typical nucleophiles; the results are nicely explained in terms of neighbouring phosphonate group participation in which the vacant p orbital strongly interacts with the phosphonate oxygen anion resulting in suppression of the availability of the vacant p orbital.

Key concepts: Phosphonate, Chemistry, Electrophile, Nucleophile, Reactivity (psychology), Group (periodic table), Ion, Stereochemistry

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