A novel strategy for the synthesis of ω-functionalized perfluoroalkyl iodides

被引：7

作者：

Szlávik, Z ^{[1
]}

Tárkányi, G ^{[1
]}

Skribanek, Z ^{[1
]}

Vass, E ^{[1
]}

Rábai, J ^{[1
]}

机构：

[1] Eotvos Lorand Univ, Dept Organ Chem, H-1518 Budapest 112, Hungary

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 15期

关键词：

D O I：

10.1021/ol0161662

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

H-(CF(2))(10)-CH(2)OH --> (5steps) I-(CF(2))(8)-CH(2)OAc The applicability of telomeric alcohols, H(CF(2)CF(2))(n)CH(2)OH, for the synthesis of omega -functionalized F-alkylating reagents, I(CF(2)CF(2))(n-1)CH(2)OAc (6, n = 5), is demonstrated. The key steps of this optimized method are the "activation" of the HCF(2)- terminus in a lithiation process yielding olefin 2 [(Z+E)-BuCF=CF(CF(2)CF(2))(4)CH(2)OH, 86%] and a successive ozonation reaction in trifluoroethanol media affording ester 3b [CF(3)CH(2)O(2)C(CF(2)CF(2))(4)CH(2)OH, 93%]. Highly stereospecific ozone cleavage of the (E)-2 isomer was observed in methanol due to the competitive oxidation of the solvent.

引用

页码：2365 / 2366

页数：2

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