N,N'-(1R,2R)-1,2-Cyclohexanediyldi(2-pyridinecarboxamide)
CAS Number:
218290-24-5
Molecular Formula:
C18H20N4O2
Mechanistic studies for dirhodium-catalyzed ring expansion reactions
Literature Information
Publication Date
2017-02-09
DOI
10.1039/C6QO00713A
Impact Factor
5.281
Authors
Yin Wei, Xu-Bo Hu, Kai Chen
View Original
Abstract
The mechanisms for dirhodium-catalyzed ring expansion reactions of azide tethered methylenecyclopropanes and their analogues were systematically investigated by DFT calculations. The calculation results indicate that the dirhodium catalyst is essential for generating a reactive Rh2–nitrene intermediate having radical character; however, it is not essential for controlling final product selectivities. For substrates involving a three-membered ring, the experimentally obtained C–N bond formation product is a thermodynamically favored product. In contrast, for substrates having a larger ring, the kinetically favored product is the main product. The DFT calculations presented here account for previous experimental findings, and throw light on other dirhodium-catalyzed reactions involving nitrene or carbene intermediates.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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Benzeneacetic acid, 2-[(2,6-dichlorophenyl)amino]-, compd. with 1-pyrrolidineethanol (1:1)
CAS Number:
119623-66-4
Molecular Formula:
C20H24Cl2N2O3
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CAS Number:
1314378-14-7
Molecular Formula:
C30H36N2O10
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