Conjugate addition with organometallics and nitration of nitroxide (aminoxyl) free radicals. Synthesis of potentially useful cross-linking spin label reagents

Kálmán Hideg, H. Olga Hankovszky, H. Anna Halász, Pál Sohár

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Abstract

3-Methoxycarbonyl-2,2,5,5-tetramethyl-2,5-dihydropyrrol-1-oxyl (1) was converted with PhMgBr-Cul in a conjugate addition into 3-methoxycarbonyl-2,2,5, 5-tetramethyl-4-phenylpyrrolidin-1-oxyl (2). Compound (2) was nitrated with concentrated H2SO4/HNO3 to give the para-nitrophenyl derivative (5). Nitration of other phenyl substituted nitroxides was also investigated. The reaction in strong acids could be carried out in the presence of an acid-sensitive nitroxide free radical. An alkyl nitro compound has also been prepared: a conjugate addition of nitromethane to (1) gave 3-methoxycarbonyl-2,2,5,5-tetramethyl-4-nitromethylpyrrolidin-1-oxyl (20). Both (2) and (20) could be transformed by transfer hydrogenation to amino compounds and then in several steps to potentially useful cross-linking spin label reagents.

Original languageEnglish
Pages (from-to)2905-2911
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number11
Publication statusPublished - Dec 1 1988

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ASJC Scopus subject areas

  • Chemistry(all)

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