The mechanism of the epoxidation of two chiral allylic alcohols, i.e., 3-methyl-3-buten-2-ol and (Z)-3-penten-2-ol, with peroxyformic acid has been investigated by locating 20 transition structures with the B3LYP/6-31G* method. The geometry of all TSs substantially conforms to a spiro (i.e., with the peroxy acid plane almost perpendicular to the CdC bond axis) butterfly orientation of the reactants while no TS resembles, even loosely, the planar butterfly structure.
Epoxidation of Acyclic chiral Allylic Alcohols with Peroxy Acids: Spiro or Planar Butterfly Transition Structures? A Computational DFT Answer.
FRECCERO, MAURO;GANDOLFI, REMO;
2000-01-01
Abstract
The mechanism of the epoxidation of two chiral allylic alcohols, i.e., 3-methyl-3-buten-2-ol and (Z)-3-penten-2-ol, with peroxyformic acid has been investigated by locating 20 transition structures with the B3LYP/6-31G* method. The geometry of all TSs substantially conforms to a spiro (i.e., with the peroxy acid plane almost perpendicular to the CdC bond axis) butterfly orientation of the reactants while no TS resembles, even loosely, the planar butterfly structure.File in questo prodotto:
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