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

Kimya Bölümü

Istanbul Technical University

Araştırma sonucu: Dergiye katkı › Makale › bilirkişi

26 Atıf (Scopus)

Özet

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.

Orijinal dil	İngilizce
Sayfa (başlangıç-bitiş)	4600-4610
Sayfa sayısı	11
Dergi	Organometallics
Hacim	27
Basın numarası	18
DOI'lar	https://doi.org/10.1021/om800094k
Yayın durumu	Yayınlandı - 22 Eyl 2008

Belgeye Erişim

10.1021/om800094k

Diğer Dosyalar ve Linkler

Link to publication in Scopus

Alıntı Yap

@article{906e28d048004fb0a95e4b50141ab63e,

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

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.",

author = "Cihan {\"O}zen and T{\"u}z{\"u}n, \{Nurcan {\c S}\}",

year = "2008",

month = sep,

day = "22",

doi = "10.1021/om800094k",

language = "English",

volume = "27",

pages = "4600--4610",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

T1 - A DFT study on the mechanism of cyclopropanation via Cu(acac) 2-catalyzed diazo ester decomposition

AU - Özen, Cihan

AU - Tüzün, Nurcan Ş

PY - 2008/9/22

Y1 - 2008/9/22

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/53849118803

U2 - 10.1021/om800094k

DO - 10.1021/om800094k

M3 - Article

AN - SCOPUS:53849118803

SN - 0276-7333

VL - 27

SP - 4600

EP - 4610

JO - Organometallics

JF - Organometallics

IS - 18