Additions of organomanganese reagents to conjugated nitroolefins

I. N.N. Namboothiri, Alfred Hassner

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Additions of organomanganese reagents to aromatic and aliphatic conjugated nitroolefins were examined for the first time. In most cases reaction proceeded rapidly at -30°C. Unlike Mn reagents lacking β-hydrogens (Me, Ph), which lead to oxidative coupling and reductive dimerisation of nitrostyrenes, benzylmanganese chloride gives 1,4-addition in yields exceeding Grignard or Cu-assisted additions. At 0°C alkyl(Bu, Pr)-manganese reagents undergo an addition-migration-elimination process with nitrostyrenes providing a convenient and stereospecific entry into arylated trans-olefins.

Original languageEnglish
Pages (from-to)69-77
Number of pages9
JournalJournal of Organometallic Chemistry
Issue number1-2
StatePublished - 12 Jul 1996

Bibliographical note

Funding Information:
Support of this research by a grant from the Israel Science Foundation is gratefully acknowledged. We thank Dr. H.E. Gottlieb for valuable help with NMR spectra.


  • Addition reaction
  • Alkenes
  • Conjugated nitroolefins
  • Manganese
  • Organomanganese reagents


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