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

The reactions of C8F17CH2CHCH2O with some primary and secondary aliphatic amines affording selective ring opening at C-beta are reported. The reactions with secondary amines (HNRR2)-R-1 (R-1 = R-2 = Et; R-1 = Bu-t, R-2 = CH2CH2O(CO)C(CH3)=CH2; R-1 = Et, R-2 = CH2CH2OH; R-1 =R-2 =CH2CH2OH) gave the corresponding C8F17CH2-CH(OH)-CH2-(NRR2)-R-1 derivatives. For R-1 = Et, R-2 = CH2CH2OH; R-1 =R-2 = 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. (c) 2005 Elsevier B.V. All rights reserved.