The Journal of Organic Chemistry

Chemistry of dioxiranes. 22. Reaction of dimethyldioxirane with alkynes

RW Murray, M Singh

Index: Murray, Robert W.; Singh, Megh Journal of Organic Chemistry, 1993 , vol. 58, # 19 p. 5076 - 5080

Full Text: HTML

Citation Number: 33

Abstract

The reaction of dimethyldioxirane with several alkynes gives products which are conveniently rationalized by postulating the intermediacy of oxirenes and oxocarbenes. The latter serve as precursors to H atom or methyl group migration products, as well as to cyclopropane insertion products in some cases. Alkenes, derived from some of these carbene reactions, are partially converted to epoxides.

 Related Synthetic Route
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~5%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

4,4-dimethylpent-1-en-3-one Structure

2177-30-2

4,4-dimethylpen...

2-hydroxy-2,3,3-trimethyl-butanoic acid Structure

4026-21-5

2-hydroxy-2,3,3...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~5%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

2,2-dimethyl-1-(oxiran-2-yl)propan-1-one Structure

128075-71-8

2,2-dimethyl-1-...

4,4-dimethylpent-1-en-3-one Structure

2177-30-2

4,4-dimethylpen...

Detail Learn More
But-2-yne Structure

503-17-3

But-2-yne

~0%

1-Oxiranylethanone Structure

4401-11-0

1-Oxiranylethanone

2,2,5,5-Tetramethyl-1,3-dioxolane-4-one Structure

4560-54-7

2,2,5,5-Tetrame...

2-Hydroxyisobutyric acid Structure

594-61-6

2-Hydroxyisobut...

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But-2-yne Structure

503-17-3

But-2-yne

Acetone Structure

67-64-1

Acetone

~0%

1-Oxiranylethanone Structure

4401-11-0

1-Oxiranylethanone

2,2,5,5-Tetramethyl-1,3-dioxolane-4-one Structure

4560-54-7

2,2,5,5-Tetrame...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~17%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

4,4-dimethylpent-1-en-3-one Structure

2177-30-2

4,4-dimethylpen...

2-hydroxy-2,3,3-trimethyl-butanoic acid Structure

4026-21-5

2-hydroxy-2,3,3...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~17%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

2,2-dimethyl-1-(oxiran-2-yl)propan-1-one Structure

128075-71-8

2,2-dimethyl-1-...

2-hydroxy-2,3,3-trimethyl-butanoic acid Structure

4026-21-5

2-hydroxy-2,3,3...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~17%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

3,4-Dimethyl-3-penten-2-one Structure

684-94-6

3,4-Dimethyl-3-...

2-hydroxy-2,3,3-trimethyl-butanoic acid Structure

4026-21-5

2-hydroxy-2,3,3...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~18%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

2,2-dimethyl-1-(oxiran-2-yl)propan-1-one Structure

128075-71-8

2,2-dimethyl-1-...

4,4-dimethylpent-1-en-3-one Structure

2177-30-2

4,4-dimethylpen...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~4%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

3,4-Dimethyl-3-penten-2-one Structure

684-94-6

3,4-Dimethyl-3-...

2-hydroxy-2,3,3-trimethyl-butanoic acid Structure

4026-21-5

2-hydroxy-2,3,3...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~3%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

2,2-dimethyl-1-(oxiran-2-yl)propan-1-one Structure

128075-71-8

2,2-dimethyl-1-...

4,4-dimethylpent-1-en-3-one Structure

2177-30-2

4,4-dimethylpen...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~9%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

4,4-dimethylpent-1-en-3-one Structure

2177-30-2

4,4-dimethylpen...

2-hydroxy-2,3,3-trimethyl-butanoic acid Structure

4026-21-5

2-hydroxy-2,3,3...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~9%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

2,2-dimethyl-1-(oxiran-2-yl)propan-1-one Structure

128075-71-8

2,2-dimethyl-1-...

2-hydroxy-2,3,3-trimethyl-butanoic acid Structure

4026-21-5

2-hydroxy-2,3,3...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~39%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

4,4-dimethylpent-1-en-3-one Structure

2177-30-2

4,4-dimethylpen...

2-hydroxy-2,3,3-trimethyl-butanoic acid Structure

4026-21-5

2-hydroxy-2,3,3...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~40%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

2,2-dimethyl-1-(oxiran-2-yl)propan-1-one Structure

128075-71-8

2,2-dimethyl-1-...

2-hydroxy-2,3,3-trimethyl-butanoic acid Structure

4026-21-5

2-hydroxy-2,3,3...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~39%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

3,4-Dimethyl-3-penten-2-one Structure

684-94-6

3,4-Dimethyl-3-...

2-hydroxy-2,3,3-trimethyl-butanoic acid Structure

4026-21-5

2-hydroxy-2,3,3...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~8%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

3,4-Dimethyl-3-penten-2-one Structure

684-94-6

3,4-Dimethyl-3-...

2-hydroxy-2,3,3-trimethyl-butanoic acid Structure

4026-21-5

2-hydroxy-2,3,3...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~8%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

2,2-dimethyl-1-(oxiran-2-yl)propan-1-one Structure

128075-71-8

2,2-dimethyl-1-...

4,4-dimethylpent-1-en-3-one Structure

2177-30-2

4,4-dimethylpen...

Detail Learn More
4,4-dimethylpent-2-yne Structure

999-78-0

4,4-dimethylpen...

~39%

1-(2,3,3-Trimethyloxirane-2-yl)ethanone Structure

15120-99-7

1-(2,3,3-Trimet...

2,2-dimethyl-1-(oxiran-2-yl)propan-1-one Structure

128075-71-8

2,2-dimethyl-1-...

4,4-dimethylpent-1-en-3-one Structure

2177-30-2

4,4-dimethylpen...

Detail Learn More

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