1,3-Dipolar cycloaddition of azomethine ylide with ethene and 2-butene: a computational study

The cycloaddition reactions of azomethine ylide with ethene, ( Z)-2-butene, and ( E)-2-butene to afford azacyclopentanes (pyrrolidines) proceed via a synchronous concerted π s 4 + π s 2 mechanism. B3LYP/6-311 + G(d,p) has been used to calculate the relative energies and geometrical parameters of the...

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Bibliographic Details
Published in:Tetrahedron letters 2005-03, Vol.46 (12), p.1993-1995
Main Authors: Freeman, Fillmore, Dang, Phuong, Huang, Angela C., Mack, Aline, Wald, Kara
Format: Article
Language:English
Subjects:
Azacyclopentane
Cycloaddition
Pyrrolidine
Transition state structure
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Summary:The cycloaddition reactions of azomethine ylide with ethene, ( Z)-2-butene, and ( E)-2-butene to afford azacyclopentanes (pyrrolidines) proceed via a synchronous concerted π s 4 + π s 2 mechanism. B3LYP/6-311 + G(d,p) has been used to calculate the relative energies and geometrical parameters of the respective reactants, transition states, and cycloadducts from the cycloadditions of azomethine ylide and ethene, ( Z)-2-butene, and ( E)-2-butene. The half-chair (envelope) transition state structures are consistent with a synchronous concerted cycloaddition mechanism.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.01.172