Premium
Selective and Shape‐Selective Baeyer–Villiger Oxidations of Aromatic Aldehydes and Cyclic Ketones with Sn‐Beta Zeolites and H 2 O 2
Author(s) -
Renz Michael,
Blasco Teresa,
Corma Avelino,
Fornés Vicente,
Jensen Robert,
Nemeth Laszlo
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20021018)8:20<4708::aid-chem4708>3.0.co;2-u
Subject(s) - chemistry , catalysis , chemoselectivity , hydrogen peroxide , baeyer–villiger oxidation , formate , alcohol oxidation , cinnamyl alcohol , zeolite , peroxide , hydrolysis , nuclear magnetic resonance spectroscopy , organic chemistry , medicinal chemistry , selectivity
Sn‐Beta is used as a heterogeneous catalyst for the Baeyer–Villiger reaction with hydrogen peroxide. Cyclic ketones are transformed into the corresponding lactones, while unsaturated ketones are oxidized to the corresponding unsaturated lactones with very high chemoselectivity. The catalyst is also selective for the oxidation of aromatic aldehydes with H 2 O 2 , producing the formate ester or the corresponding hydrolyzed product, that is the alcohol. Shape‐selective oxidations are observed for isomeric reactants with different molecular shapes. The catalytic Sn sites have been characterized by 119 Sn MAS‐NMR spectroscopy, and tetrahedral incorporation into the zeolite framework has been demonstrated. In situ IR spectroscopy and 18 O labeling experiments have shown that the oxidation mechanism involves an intermediate of the Criegee type.