title: Reaction of nitrones with silyl ketene acetals: a DFT study.
abstract: Theoretical calculations at the DFT level indicate that the reaction of a nitrone with a silyl ketene acetal proceeds, contrary to previous suggestions, through a classical 1,3-dipolar cycloaddition, followed by a silyl group transfer step to give the open-chain product. Introduction of a diffuse basis set is necessary to describe properly nitrones. The influence of a Lewis acid has been studied.
authors.affiliation: Chimie Recherche (LEDSS), Université Joseph Fourier, BP53, 38041 Grenoble, France.
authors.forename: Anne
authors.initials: A
authors.lastname: Milet
authors.forename: Yves
authors.initials: Y
authors.lastname: Gimbert
authors.forename: Andrew E
authors.initials: AE
authors.lastname: Greene
mesh_terms: D000080:Acetals / Q000737:chemistry*; D003198:Computer Simulation; D005030:Ethylenes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory; D012821:Silanes / Q000737:chemistry*
chemical_list: D000080:Acetals; D005030:Ethylenes; D007659:Ketones; D009589:Nitrogen Oxides; D009942:Organometallic Compounds; D012821:Silanes; C015388:nitrones; C008223:ketene