Abstract
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 language | English |
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Pages (from-to) | 69-77 |
Number of pages | 9 |
Journal | Journal of Organometallic Chemistry |
Volume | 518 |
Issue number | 1-2 |
DOIs | |
State | Published - 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.
Keywords
- Addition reaction
- Alkenes
- Conjugated nitroolefins
- Manganese
- Organomanganese reagents