The Journal of Organic Chemistry

A novel oxidation of internal alkynes with hydrogen peroxide catalyzed by peroxotungsten compounds

Y Ishii, Y Sakata

Index: Ishii, Yasutaka; Sakata, Yasuyuki Journal of Organic Chemistry, 1990 , vol. 55, # 21 p. 5545 - 5547

Full Text: HTML

Citation Number: 82

Abstract

Summary: Internal alkynes underwent a novel oxidation with aqueous hydrogen peroxide catalyzed by peroxotungsten compounds under two-phase conditions using chloroform as the solvent, giving a,@-epoxy ketones and a,@-unsaturated ketones as principal products. The epoxidation of a, p-unsaturated ketones by this catalyst-oxidant system appeared to involve the electrophilic attack of the peroxo species to the double bond.

 Related Synthetic Route
2-Octyne Structure

2809-67-8

2-Octyne

~7%

1-(3-Butyloxiranyl)ethanone Structure

17257-80-6

1-(3-Butyloxira...

1-Octen-3-one Structure

4312-99-6

1-Octen-3-one

(E)-Oct-3-en-2-one Structure

18402-82-9

(E)-Oct-3-en-2-one

Detail
4-Octyne Structure

1942-45-6

4-Octyne

~14%

oct-5-en-4-one Structure

30647-85-9

oct-5-en-4-one

α,β-epoxy-4-octanone Structure

5162-93-6

α,β-epoxy-4-octanone

Butyric Acid Structure

107-92-6

Butyric Acid

2-Octyne Structure

2809-67-8

2-Octyne

~14%

1-(3-Butyloxiranyl)ethanone Structure

17257-80-6

1-(3-Butyloxira...

1-Octen-3-one Structure

4312-99-6

1-Octen-3-one

(E)-Oct-3-en-2-one Structure

18402-82-9

(E)-Oct-3-en-2-one

Detail
2-Octyne Structure

2809-67-8

2-Octyne

~13%

1-(3-Butyloxiranyl)ethanone Structure

17257-80-6

1-(3-Butyloxira...

(E)-Oct-3-en-2-one Structure

18402-82-9

(E)-Oct-3-en-2-one

1,2-epoxy-3-octanone Structure

114701-53-0

1,2-epoxy-3-octanone

Detail
2-Octyne Structure

2809-67-8

2-Octyne

~41%

1-(3-Butyloxiranyl)ethanone Structure

17257-80-6

1-(3-Butyloxira...

1-Octen-3-one Structure

4312-99-6

1-Octen-3-one

(E)-Oct-3-en-2-one Structure

18402-82-9

(E)-Oct-3-en-2-one

Detail
3-Octyne Structure

15232-76-5

3-Octyne

~55%

1-(3-propyloxiran-2-yl)propan-1-one Structure

6124-59-0

1-(3-propyloxir...

N/A Structure

22286-99-3

N/A

N/A Structure

119163-22-3

N/A

Detail
3-Octyne Structure

15232-76-5

3-Octyne

~58%

1-(3-propyloxiran-2-yl)propan-1-one Structure

6124-59-0

1-(3-propyloxir...

N/A Structure

22286-99-3

N/A

N/A Structure

119163-22-3

N/A

Detail
2-Octyne Structure

2809-67-8

2-Octyne

~38%

1-(3-Butyloxiranyl)ethanone Structure

17257-80-6

1-(3-Butyloxira...

(E)-Oct-3-en-2-one Structure

18402-82-9

(E)-Oct-3-en-2-one

1,2-epoxy-3-octanone Structure

114701-53-0

1,2-epoxy-3-octanone

Detail

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