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

被引：12

作者：

Conte, L

Maniero, F

Zaggia, A

Bertani, R

Garnbaretto, G

Berton, A

Seraglia, R

机构：

[1] Univ Padua, Dipartimento Proc Chim Ingn, I-35131 Padua, Italy

[2] Univ Padua, Ist Sci & Tecnol Mol, CNR, I-35131 Padua, Italy

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2005年 / 126卷 / 9-10期

关键词：

(perfuoroalkyl)methyl]oxiranes; F-alkyl oxiranes; ring opening; primary and secondary aliphatic amines; aminoalcohols; fluorinated surfactants;

D O I：

10.1016/j.jfluchem.2005.06.002

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

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.

引用

页码：1274 / 1280

页数：7

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