Additions of organomanganese reagents to conjugated nitroolefins

I. N.N. Namboothiri; Alfred Hassner

doi:10.1016/0022-328x(96)06150-5

Additions of organomanganese reagents to conjugated nitroolefins

I. N.N. Namboothiri, Alfred Hassner

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

29 Scopus citations

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
Pages (from-to)	69-77
Number of pages	9
Journal	Journal of Organometallic Chemistry
Volume	518
Issue number	1-2
DOIs	https://doi.org/10.1016/0022-328x(96)06150-5
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.

Funding

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.

Funders	Funder number
Israel Science Foundation

Keywords

Addition reaction
Alkenes
Conjugated nitroolefins
Manganese
Organomanganese reagents

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10.1016/0022-328x(96)06150-5

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title = "Additions of organomanganese reagents to conjugated nitroolefins",

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.",

keywords = "Addition reaction, Alkenes, Conjugated nitroolefins, Manganese, Organomanganese reagents",

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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.",

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AU - Namboothiri, I. N.N.

AU - Hassner, Alfred

N1 - 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.

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N2 - 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.

AB - 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.

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Additions of organomanganese reagents to conjugated nitroolefins

Abstract

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Keywords

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