Regioselective ring opening of [(perfluoroalkyl)methyl] oxiranes with N-nucleophiles

The reactions of with some primary and secondary aliphatic amines affording selective ring opening at Cβ are reported. The reactions with secondary amines HNR1R2 (R1 = R2 = Et; R1 = But, R2 = CH2CH2O(CO)C(CH3)CH2; R1 = Et, R2 = CH2CH2OH; R1 = R2 = CH2CH2OH) gave the corresponding C8F17CH2CH(OH)CH2NR1R2 derivatives. For R1 = Et, R2 = CH2CH2OH; R1 = R2 = CH2CH2OH, the reactions proceed through the selective nucleophilic attack of the NH moiety with no evidence of reactivity of the OH group. The reactions with the primary amines, allylamine and n-hexamethylenediamine, gave different products depending on reaction conditions.