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

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.

Keywords

Addition reaction
Alkenes
Conjugated nitroolefins
Manganese
Organomanganese reagents

Access to Document

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

Cite this

@article{e5e1859c624e4cec93030577604b8c59,

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",

author = "Namboothiri, {I. N.N.} and Alfred Hassner",

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.",

year = "1996",

month = jul,

day = "12",

doi = "10.1016/0022-328X(96)06150-5",

language = "אנגלית",

volume = "518",

pages = "69--77",

journal = "Journal of Organometallic Chemistry",

issn = "0022-328X",

publisher = "Elsevier",

number = "1-2",

}

TY - JOUR

T1 - Additions of organomanganese reagents to conjugated nitroolefins

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.

PY - 1996/7/12

Y1 - 1996/7/12

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.

KW - Addition reaction

KW - Alkenes

KW - Conjugated nitroolefins

KW - Manganese

KW - Organomanganese reagents

UR - http://www.scopus.com/inward/record.url?scp=0030581056&partnerID=8YFLogxK

U2 - 10.1016/0022-328X(96)06150-5

DO - 10.1016/0022-328X(96)06150-5

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:0030581056

SN - 0022-328X

VL - 518

SP - 69

EP - 77

JO - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

IS - 1-2

ER -

Additions of organomanganese reagents to conjugated nitroolefins

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this