Ipso Nitration. An Efficient Synthesis of Ipso Nitration Products of Aromatic Hydrocarbons

C. E. Barnes, K. S. Feldman, M. W. Johnson, H. W.H. Lee, P. C. Myhre

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)3925-3930
Number of pages6
JournalJournal of Organic Chemistry
Volume44
Issue number22
DOIs
StatePublished - Jan 1 1979

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Barnes, C. E., Feldman, K. S., Johnson, M. W., Lee, H. W. H., & Myhre, P. C. (1979). Ipso Nitration. An Efficient Synthesis of Ipso Nitration Products of Aromatic Hydrocarbons. Journal of Organic Chemistry, 44(22), 3925-3930. https://doi.org/10.1021/jo01336a034