Double- and triple-consecutive O-insertion into tert-butyl and triarylmethyl structures

Pavel A. Krasutsky, Igor V Kolomitsyn, Sergiy G. Krasutsky, Paul Kiprof

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

(Matrix Presented) 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°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.

Original languageEnglish (US)
Pages (from-to)2539-2542
Number of pages4
JournalOrganic Letters
Volume6
Issue number15
DOIs
StatePublished - Jul 22 2004

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