Oxidative cleavage of p-methoxybenzyl ethers with methyl(trifluoromethyl)dioxirane.
[reaction: see text] The ability of methyl(trifluoromethyl)dioxirane to cleave p-methoxylbenzyl ethers oxidatively in the presence of various additional functional groups has been investigated. These reactions, performed in aqueous acetonitrile, transform a reasonably robust aryl substituent into a dienyl aldehydo ester. The originally generated E,Z-isomer undergoes slow conversion to the more stable E,E-form at 20 degrees C.
Paquette
Leo A
LA
Evans Chemical Laboratories, Ohio State University, Columbus, Ohio 43210, USA. paquette.l@osu.edu
Kreilein
Matthew M
MM
Bedore
Matthew W
MW
Friedrich
Dirk
D