Premium
Baeyer–Villiger Oxidations with Hydrogen Peroxide in Fluorinated Alcohols: Lactone Formation by a Nonclassical Mechanism
Author(s) -
Berkessel Albrecht,
Andreae Marc R. M.,
Schmickler Hans,
Lex Johann
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20021202)41:23<4481::aid-anie4481>3.0.co;2-7
Subject(s) - cyclohexanone , chemistry , hydrogen peroxide , lactone , solvent , catalysis , baeyer–villiger oxidation , organic chemistry , exothermic reaction
What a difference the solvent makes! Unlike in conventional solvents, nonstrained ketones such as cyclohexanone react smoothly with hydrogen peroxide in 1,1,1,3,3,3‐hexafluoro‐2‐propanol (HFIP) to give lactones. The reaction proceeds via an isolatable spiro‐bisperoxide, which undergoes a highly exothermic acid‐catalyzed rearrangement to two equivalents of lactone (see Equation and IR thermogram).