Oxaziridines are commonly employed for the epoxidation of olefins, for the oxidation of organometallic species and organo-sulfur, -selenium, -nitrogen compounds, but they have not been used in the oxidation of alcohols. We will describe how perfluorinated oxaziridines can be used for the clean and high yield transformation of secondary alcohols into corresponding ketones. It has been found that perfluoro 2-n-butyl-3-n-propyloxaziridine 1 (prepared in two steps from perfluoro tributylamine) afforded acetone 2 in nearly quantitative yield when reacted with 2-propanol. Similar clean reactions have been observed for more complex substrates such as ethyl lactate, fenchyl alcohol, and androsterone which afforded ethyl pyruvate 3, fenchone 4, and androstanedione 5, respectively. The generality of the process will be presented and reaction conditions employed will be discussed in detail.
Oxidative properties of fluorinated oxaziridines
RESNATI, GIUSEPPE
1992-01-01
Abstract
Oxaziridines are commonly employed for the epoxidation of olefins, for the oxidation of organometallic species and organo-sulfur, -selenium, -nitrogen compounds, but they have not been used in the oxidation of alcohols. We will describe how perfluorinated oxaziridines can be used for the clean and high yield transformation of secondary alcohols into corresponding ketones. It has been found that perfluoro 2-n-butyl-3-n-propyloxaziridine 1 (prepared in two steps from perfluoro tributylamine) afforded acetone 2 in nearly quantitative yield when reacted with 2-propanol. Similar clean reactions have been observed for more complex substrates such as ethyl lactate, fenchyl alcohol, and androsterone which afforded ethyl pyruvate 3, fenchone 4, and androstanedione 5, respectively. The generality of the process will be presented and reaction conditions employed will be discussed in detail.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
