A DFT study on the mechanism of cyclopropanation via Cu(acac) 2-catalyzed diazo ester decomposition

Cihan Özen; Nurcan Ş Tüzün

doi:10.1021/om800094k

A DFT study on the mechanism of cyclopropanation via Cu(acac) ₂-catalyzed diazo ester decomposition

Cihan Özen, Nurcan Ş Tüzün

Department of Chemistry

Istanbul Technical University

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

The mechanism of the copper(I)-catalyzed olefin cyclopropanation reaction with dimethyl diazomalonate has been extensively investigated using the DFT method at B3LYP/6-31G* and BP86/SDD/6-31G* levels. AU the possible pathways leading first to a metal carbene and then to the cyclopropane product have been studied with ethene as a model substrate and their energetics are demonstrated. Then the suggested mechanisms were applied to a real system: namely, 2,2-dimethyl-4,7-dihydro-1,3-dioxepine.

Original language	English
Pages (from-to)	4600-4610
Number of pages	11
Journal	Organometallics
Volume	27
Issue number	18
DOIs	https://doi.org/10.1021/om800094k
Publication status	Published - 22 Sept 2008

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abstract = "The mechanism of the copper(I)-catalyzed olefin cyclopropanation reaction with dimethyl diazomalonate has been extensively investigated using the DFT method at B3LYP/6-31G* and BP86/SDD/6-31G* levels. AU the possible pathways leading first to a metal carbene and then to the cyclopropane product have been studied with ethene as a model substrate and their energetics are demonstrated. Then the suggested mechanisms were applied to a real system: namely, 2,2-dimethyl-4,7-dihydro-1,3-dioxepine.",

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ER -

A DFT study on the mechanism of cyclopropanation via Cu(acac) ₂-catalyzed diazo ester decomposition

Abstract

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