Perfluorinated oxaziridines are known to hydroxylate unactivated hydrocarbons with remarkable regio , and diastereospecificity . This is a highly coveted transformation , and similar reactivity and specificity is seldom rivaled , especially considering the nonmetallic nature of the oxidant . Perfluorinated oxaziridines show high selectivity toward tertiary hydrogens . Hydroxylation of primary carbons and dihydroxylation of a compound with two oxidizable sites have never been observed . Retention of stereochemistry is very high , often 95 - 98 % . ( retenton of stereochemistry may be further enhanced by the addition of a fluoride salt ) .