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2010 | 8 | 1 | 223-228
Tytuł artykułu

DFT investigation on mechanism of dirhodium tetracarboxylate-catalyzed O-H insertion of diazo compounds with H2O

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The mechanism of the dirhodium tetracarboxylate-catalyzed O-H insertion reaction of diazomethane and methyl diazoacetate with H2O has been studied in detail using DFT calculations. The rhodium catalyst and a diazo compound couple to form a rhodiumcarbene complex. Of two reaction pathways of the Rh(II)-carbene complex with H2O, the stepwise pathway is more preferable than the concerted one. Formation of a Rh(II) complex-associated oxonium ylide is an exothermal process, and direct decomposition of the ylide gives a very high barrier. The high barriers for the 1,2-H shift of Rh(II) complex-associated oxonium ylides make the ylides become stable intermediates in both reactions, especially for the reactions in solution. Difficulty in formation of a free oxonium ylide supports experimental results, indicating that the Rh(II) complex-catalyzed nucleophilic addition of a diazo compound proceeds via a Rh(II) complex-associated oxonium ylide rather than via a free oxonium ylide. [...]
Wydawca

Czasopismo
Rocznik
Tom
8
Numer
1
Strony
223-228
Opis fizyczny
Daty
wydano
2010-02-01
online
2010-02-16
Twórcy
autor
  • Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, People’s Republic of China, 116023, beam@dicp.ac.cn
autor
  • Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, People’s Republic of China, 116023
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Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_s11532-009-0118-8
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