IPSO NITRATION - EFFICIENT SYNTHESIS OF IPSO NITRATION PRODUCTS OF AROMATIC-HYDROCARBONS

被引:28
作者
BARNES, CE [1 ]
FELDMAN, KS [1 ]
JOHNSON, MW [1 ]
LEE, HWH [1 ]
MYHRE, PC [1 ]
机构
[1] HARVEY MUDD COLL,DEPT CHEM,CLAREMONT,CA 91711
关键词
D O I
10.1021/jo01336a034
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Ipso nitration products of aromatic hydrocarbons have been synthesized from phenols. Nitration of a number of 4-alkylphenyl acetates gave 4-alkyl-4-nitrocyclohexadienones. Reduction of these nitrodienones with sodium borohydride in methanol gave 4-alkyl-4-nitrocyclohexadienols. These labile nitrodienols were converted to the more easily handled 4-alkyl-4-nitrocyclohexadienyl acetates by low-temperature acylation with acetyl chloride and pyridine. Representative nitrodienyl acetates were synthesized by this three-step sequence in 60% yield from the starting phenyl acetate. The synthesis of l, 4-dimethyl-4-nitrocyclohexadienol from 4-methyl-4-nitrocyclohexadienone illustrates the use of organolithium reagents in 1, 2-addition to the carbonyl center of nitrodienones. © 1979, American Chemical Society. All rights reserved.
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页码:3925 / 3930
页数:6
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