Double- and triple-consecutive O-insertion into tert-butyl and triarylmethyl structures.
[reaction: see text] The concecutive Criegee rearrangement reactions were studied for tert-butyl trifluoroacetate, triarylcarbinols, and benzophenone ketales with trifluoroperacetic acid (TFPAA) in trifluoroacetic acid (TFA). The formation of methyl acetate and methyl trifluoroacetate indicates that the consecutive double-O-insertion process has taken place for tert-butyl trifluoroacetate. The intermediate dimethoxymethylcarbonium ion was detected below 5 degrees C. A consecutive triple-O-insertion process has been observed for triarylmethanols and benzophenone ketals. A new high yield method of corresponding diaryl carbonates synthesis was developed.
Krasutsky
Pavel A
PA
Natural Resources Research Institute, 5013 Miller Trunk Highway, Duluth, Minnesota 55811-1442, USA. pkrasuts@d.umn.edu
Kolomitsyn
Igor V
IV
Krasutsky
Sergiy G
SG
Kiprof
Paul
P