19386-06-2Relevant articles and documents
Interrupted Baeyer–Villiger Rearrangement: Building A Stereoelectronic Trap for the Criegee Intermediate
Vil', Vera A.,dos Passos Gomes, Gabriel,Bityukov, Oleg V.,Lyssenko, Konstantin A.,Nikishin, Gennady I.,Alabugin, Igor V.,Terent'ev, Alexander O.
, p. 3372 - 3376 (2018)
The instability of hydroxy peroxyesters, the elusive Criegee intermediates of the Baeyer–Villiger rearrangement, can be alleviated by selective deactivation of the stereoelectronic effects that promote the 1,2-alkyl shift. Stable cyclic Criegee intermediates constrained within a five-membered ring can be prepared by mild reduction of the respective hydroperoxy peroxyesters (β-hydroperoxy-β-peroxylactones) which were formed in high yields in reaction of β-ketoesters with BF3?Et2O/H2O2.