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

Akio Toshimitsu; Hiroto Owada; Keiji Terao; Sakae Uemura; Masaya Okano

doi:10.1021/jo00194a024

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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Organoselenium chemistry. .alpha.-Phenylseleno carbonyl compounds as precursors for .alpha.,.beta.-unsaturated ketones and esters

Journal of the American Chemical Society ◽

10.1021/ja00798a090 ◽

1973 ◽

Vol 95 (17) ◽

pp. 5813-5815 ◽

Cited By ~ 174

Author(s):

Hans J. Reich ◽

Ieva L. Reich ◽

James M. Renga

Keyword(s):

Carbonyl Compounds ◽

Unsaturated Ketones ◽

Alpha Beta

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Magnesium Salt-Induced Opening of α, β-Epoxy Sulfoxides : A Synthesis of α-Chloro Ketones, α-Alkoxy Ketones, and α, β-Unsaturated Ketones from Carbonyl Compounds through α, β-Epoxy Sulfoxides

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.35.4632 ◽

1987 ◽

Vol 35 (11) ◽

pp. 4632-4636 ◽

Cited By ~ 5

Author(s):

TSUYOSHI SATOH ◽

ATSUSHI SUGIMOTO ◽

KOJI YAMAKAWA

Keyword(s):

Carbonyl Compounds ◽

Magnesium Salt ◽

Unsaturated Ketones ◽

Alpha Beta

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ChemInform Abstract: CHLORINATION OF ALPHA,BETA-UNSATURATED CARBONYL COMPOUNDS PART 5, MECHANISM OF CHLORINATION OF ALPHA,BETA-UNSATURATED KETONES IN METHANOL AND IN TRIFLUOROACETIC ACID

Chemischer Informationsdienst ◽

10.1002/chin.197424188 ◽

1974 ◽

Vol 5 (24) ◽

pp. no-no

Author(s):

MERCEDES C. CABALEIRO ◽

ALICIA B. CHOPA

Keyword(s):

Trifluoroacetic Acid ◽

Carbonyl Compounds ◽

Unsaturated Ketones ◽

Alpha Beta

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ChemInform Abstract: ORGANOMETALLIC REAGENTS IN ORGANIC SYNTHESIS PART 1, MECHANISTIC ASPECTS OF THE CONJUGATE ADDITION REACTIONS OF ORGANOCOPPER REAGENTS TO ALPHA,BETA UNSATURATED KETONES

Chemischer Informationsdienst ◽

10.1002/chin.197516439 ◽

1975 ◽

Vol 6 (16) ◽

pp. no-no

Author(s):

D. J. HANNAH ◽

R. A. J. SMITH

Keyword(s):

Organic Synthesis ◽

Conjugate Addition ◽

Addition Reactions ◽

Organometallic Reagents ◽

Unsaturated Ketones ◽

Alpha Beta

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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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ChemInform Abstract: PYRIDYLSELENO GROUP IN ORGANIC SYNTHESIS. PREPARATION AND OXIDATION OF α-(2-PYRIDYLSELENO) CARBONYL COMPOUNDS LEADING TO α,β-UNSATURATED KETONES AND ALDEHYDES

Chemischer Informationsdienst ◽

10.1002/chin.198511160 ◽

1985 ◽

Vol 16 (11) ◽

Author(s):

A. TOSHIMITSU ◽

H. OWADA ◽

K. TERAO ◽

S. UEMURA ◽

M. OKANO

Keyword(s):

Organic Synthesis ◽

Carbonyl Compounds ◽

Unsaturated Ketones

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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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ChemInform Abstract: ORGANOSELENIUM CHEMISTRY, ALPHA-PHENYLSELENO CARBONYL COMPOUNDS AS PRECURSORS FOR ALPHA,BETA-UNSATURATED KETONES AND ESTERS

Chemischer Informationsdienst ◽

10.1002/chin.197343348 ◽

1973 ◽

Vol 4 (43) ◽

pp. no-no

Author(s):

HANS J. REICH ◽

IEVA L. REICH ◽

JAMES M. RENGA

Keyword(s):

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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