Binuclear clusters in organic synthesis. Synthetic and mechanistic studies of the reduction of .alpha.,.beta.-unsaturated carbonyl compounds by sodium hydrogen octacarbonyldiferrate

James P. Collman; Richard G. Finke; Paul L. Matlock; Robert Wahren; John I. Brauman

doi:10.1021/ja00431a078

Binuclear clusters in organic synthesis. Synthetic and mechanistic studies of the reduction of .alpha.,.beta.-unsaturated carbonyl compounds by sodium hydrogen octacarbonyldiferrate

Journal of the American Chemical Society ◽

10.1021/ja00431a078 ◽

1976 ◽

Vol 98 (15) ◽

pp. 4685-4687 ◽

Cited By ~ 22

Author(s):

James P. Collman ◽

Richard G. Finke ◽

Paul L. Matlock ◽

Robert Wahren ◽

John I. Brauman

Keyword(s):

Organic Synthesis ◽

Carbonyl Compounds ◽

Mechanistic Studies ◽

Sodium Hydrogen ◽

Alpha Beta

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Synthetic and mechanistic studies of the reduction of .alpha.,.beta.-unsaturated carbonyl compounds by the binuclear cluster, sodium hydrogen octacarbonyldiferrate

Journal of the American Chemical Society ◽

10.1021/ja00472a016 ◽

1978 ◽

Vol 100 (4) ◽

pp. 1119-1140 ◽

Cited By ~ 89

Author(s):

James P. Collman ◽

Richard G. Finke ◽

Paul L. Matlock ◽

Robert Wahren ◽

Robert G. Komoto ◽

...

Keyword(s):

Carbonyl Compounds ◽

Mechanistic Studies ◽

Binuclear Cluster ◽

Sodium Hydrogen ◽

Alpha Beta

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ChemInform Abstract: BINUCLEAR CLUSTERS IN ORGANIC SYNTHESIS. SYNTHETIC AND MECHANISTIC STUDIES OF THE REDUCTION OF α,β-UNSATURATED CARBONYL COMPOUNDS BY SODIUM HYDROGEN OCTACARBONYLDIFERRATE

Chemischer Informationsdienst ◽

10.1002/chin.197642137 ◽

1976 ◽

Vol 7 (42) ◽

pp. no-no

Author(s):

JAMES P. COLLMAN ◽

RICHARD G. FINKE ◽

PAUL L. MATLICK ◽

ROBERT WAHREN ◽

JOHN I. BRAUMAN

Keyword(s):

Organic Synthesis ◽

Carbonyl Compounds ◽

Mechanistic Studies ◽

Sodium Hydrogen

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.alpha.,.beta.-Epoxy sulfoxides as useful intermediates in organic synthesis. 22. Stereospecific desulfinylation of sulfinylaziridines with alkylmetals: a novel synthesis including asymmetric synthesis of (Z)-N-arylaziridines and some mechanistic studies

The Journal of Organic Chemistry ◽

10.1021/jo00277a041 ◽

1989 ◽

Vol 54 (16) ◽

pp. 3973-3978 ◽

Cited By ~ 71

Author(s):

Tsuyoshi Satoh ◽

Takahiko Sato ◽

Teruhiko Oohara ◽

Koji Yamakawa

Keyword(s):

Asymmetric Synthesis ◽

Organic Synthesis ◽

Mechanistic Studies ◽

Novel Synthesis ◽

Alpha Beta

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ChemInform Abstract: SYNTHETIC AND MECHANISTIC STUDIES OF THE REDUCTION OF α,β-UNSATURATED CARBONYL COMPOUNDS BY THE BINUCLEAR CLUSTER, SODIUM HYDROGEN OCTACARBONYLDIFERRATE

Chemischer Informationsdienst ◽

10.1002/chin.197823279 ◽

1978 ◽

Vol 9 (23) ◽

Author(s):

J. P. COLLMAN ◽

R. G. FINKE ◽

P. L. MATLOCK ◽

R. WAHREN ◽

R. G. KOMOTO ◽

...

Keyword(s):

Carbonyl Compounds ◽

Mechanistic Studies ◽

Binuclear Cluster ◽

Sodium Hydrogen

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.alpha.,.beta.-Epoxy sulfoxides as useful intermediates in organic synthesis. 21. A novel approach to the asymmetric synthesis of epoxides, allylic alcohols, .alpha.-amino ketones, and .alpha.-amino aldehydes from carbonyl compounds through .alpha.,.beta.-epoxy sulfoxides using the optically active p-tolylsulfinyl group to induce chirality

The Journal of Organic Chemistry ◽

10.1021/jo00274a032 ◽

1989 ◽

Vol 54 (13) ◽

pp. 3130-3136 ◽

Cited By ~ 97

Author(s):

Tsuyoshi Satoh ◽

Teruhiko Oohara ◽

Yoshiko Ueda ◽

Koji Yamakawa

Keyword(s):

Asymmetric Synthesis ◽

Organic Synthesis ◽

Carbonyl Compounds ◽

Optically Active ◽

Allylic Alcohols ◽

Amino Aldehydes ◽

Novel Approach ◽

Alpha Beta

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Ultrasound in organic synthesis. 7. Preparation of organozinc reagents and their nickel-catalyzed reactions with .alpha.,.beta.-unsaturated carbonyl compounds

The Journal of Organic Chemistry ◽

10.1021/jo00350a065 ◽

1985 ◽

Vol 50 (26) ◽

pp. 5761-5765 ◽

Cited By ~ 71

Author(s):

Christian Petrier ◽

Jayne De Souza Barbosa ◽

Claude Dupuy ◽

Jean Louis Luche

Keyword(s):

Organic Synthesis ◽

Carbonyl Compounds ◽

Alpha Beta ◽

Catalyzed Reactions ◽

Organozinc Reagents

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Pyridylseleno group in organic synthesis. Preparation and oxidation of .alpha.-(2-pyridylseleno) carbonyl compounds leading to .alpha.,.beta.-unsaturated ketones and aldehydes

The Journal of Organic Chemistry ◽

10.1021/jo00194a024 ◽

1984 ◽

Vol 49 (20) ◽

pp. 3796-3800 ◽

Cited By ~ 55

Author(s):

Akio Toshimitsu ◽

Hiroto Owada ◽

Keiji Terao ◽

Sakae Uemura ◽

Masaya Okano

Keyword(s):

Organic Synthesis ◽

Carbonyl Compounds ◽

Unsaturated Ketones ◽

Alpha Beta

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One-Pot, Regioselective Synthesis of Homopropargyl Alcohols using Propargyl Bromide and Carbonyl Compound by the Mg-mediated Reaction under Solvent-free Conditions

Letters in Organic Chemistry ◽

10.2174/1570178616666190926104037 ◽

2020 ◽

Vol 17 (6) ◽

pp. 438-442

Author(s):

Xiaofang Ma ◽

Shunxi Li ◽

Samrat Devaramani ◽

Guohu Zhao ◽

Daqian Xu

Keyword(s):

Reaction Time ◽

Organic Synthesis ◽

Carbonyl Compounds ◽

Solvent Free ◽

Propargyl Bromide ◽

Important Goal ◽

One Pot ◽

Short Reaction Time ◽

Solvent Free Conditions ◽

Volatile Organic

The elimination of volatile organic solvents in organic synthesis is the most important goal in “Green” chemistry. We report a simple, efficient and facile method for the addition of progargyl bromide to carbonyl compounds using Mg metal as a mediator under solvent-free conditions which could regioselectively generate homopropargyl alcohols efficiently in good to excellent yields. The procedure has advantages such as short reaction time, operationally simple, excellent product yields, high regioselectivity and organic solvent-free.

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