NEW ALKANE FUNCTIONALIZATION REACTIONS BASED ON GIF-TYPE CHEMISTRY IN THE PRESENCE OF ALKALI-METAL SALTS

被引：20
作者：
BARTON, DHR
BEVIERE, SD
CHAVASIRI, W
DOLLER, D
HU, B
机构：
[1] Department of Chemistry, Texas A and M University, College Station
来源：
TETRAHEDRON LETTERS | 1993年 / 34卷 / 12期
基金：
美国国家科学基金会;
关键词：
D O I：
10.1016/S0040-4039(00)91950-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cycloalkanes are transformed into monosubstituted cycloalkyl derivatives (chloride, azide, cyanide, thiocyanate, dicycloalkyl disulfide, or nitroalkane) in mostly good efficiencies by treatment with tert-butyl hydroperoxide in pyridine/acetic acid containing Fe(NO3)3.9H2O, in the presence of alkali metal salts (LiCl, NaN3,[Et4N]CN, NaSCN, Na2S, or NaNO2, respectively). In comparison, ionic trapping with Cu(OAc)2 gave efficient trapping with chloride ion, very inefficient capture of thiocyanate, and a significant difference in reactivity towards azide ion.
引用
收藏
页码：1871 / 1874
页数：4
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