Journal of the American Chemical Society

Organic reactions catalyzed by methylrhenium trioxide: Reactions of ethyl diazoacetate and organic azides

Z Zhu, JH Espenson

Index: Zhu, Zuolin; Espenson, James H. Journal of the American Chemical Society, 1996 , vol. 118, # 41 p. 9901 - 9907

Full Text: HTML

Citation Number: 103

Abstract

Methylrhenium trioxide (CH3ReO3 or MTO) catalyzes several classes of reactions of ethyl diazoacetate, EDA. It is the first high valent oxo complex for carbene transfer. Under mild conditions and in the absence of other substrates, EDA was converted to a 9: 1 mixture of diethyl maleate and diethyl fumarate. In the presence of alcohols, α-alkoxy ethyl acetates were obtained in good yield. The yields dropped for the larger and more branched ...

 Related Synthetic Route
EDA Structure

623-73-4

EDA

tert-Butylamine Structure

75-64-9

tert-Butylamine

~81%

ethyl 2-(tert-butylamino)acetate Structure

37885-76-0

ethyl 2-(tert-b...

EDA Structure

623-73-4

EDA

Hexylamine Structure

111-26-2

Hexylamine

~89%

Glycine, N-hexyl-,ethyl ester Structure

76991-23-6

Glycine, N-hexy...

3-Methyl-2-butanone Structure

563-80-4

3-Methyl-2-butanone

EDA Structure

623-73-4

EDA

~47%

Oxiranecarboxylic acid, 3-methyl-3-(1-methylethyl)-, ethyl ester (9CI) Structure

274689-93-9

Oxiranecarboxyl...

EDA Structure

623-73-4

EDA

4-Ethylphenol Structure

123-07-9

4-Ethylphenol

~91%

ethyl 2-(4-ethylphenoxy)acetate Structure

71475-45-1

ethyl 2-(4-ethy...

EDA Structure

623-73-4

EDA

tetramethylethylene Structure

563-79-1

tetramethylethylene

~55%

Ethyl 2,2,3,3-tetramethylcyclopropane-carboxylate Structure

771-10-8

Ethyl 2,2,3,3-t...

4-Nitrobenzaldehyde Structure

555-16-8

4-Nitrobenzaldehyde

Benzene, azido- Structure

622-37-7

Benzene, azido-

~92%

Benzenamine,N-[(4-nitrophenyl)methylene]- Structure

785-80-8

Benzenamine,N-[...

EDA Structure

623-73-4

EDA

Heptan-1-ol Structure

111-70-6

Heptan-1-ol

~81%

ethyl n-heptyloxyacetate Structure

3938-81-6

ethyl n-heptylo...

EDA Structure

623-73-4

EDA

p-Cresol Structure

106-44-5

p-Cresol

~89%

cherry oxyacetate Structure

67028-40-4

cherry oxyacetate

4-Methoxybenzaldehyde Structure

123-11-5

4-Methoxybenzal...

Benzene, azido- Structure

622-37-7

Benzene, azido-

~89%

N-(4-Methoxybenzylidene)aniline Structure

836-41-9

N-(4-Methoxyben...

EDA Structure

623-73-4

EDA

Mequinol Structure

150-76-5

Mequinol

~91%

Acetic acid,2-(4-methoxyphenoxy)-, ethyl ester Structure

18598-23-7

Acetic acid,2-(...

EDA Structure

623-73-4

EDA

4-Chlorophenol Structure

106-48-9

4-Chlorophenol

~84%

Ethyl p-Chlorophenoxyacetate Structure

14426-42-7

Ethyl p-Chlorop...

EDA Structure

623-73-4

EDA

Methanol Structure

67-56-1

Methanol

~90%

Ethyl methoxyacetate Structure

3938-96-3

Ethyl methoxyacetate

EDA Structure

623-73-4

EDA

Acetophenone Structure

98-86-2

Acetophenone

~58%

Ethyl methylphenylglycidate Structure

77-83-8

Ethyl methylphe...

Benzaldehyde Structure

100-52-7

Benzaldehyde

Benzene, azido- Structure

622-37-7

Benzene, azido-

~91%

Benzylideneaniline Structure

538-51-2

Benzylideneaniline

EDA Structure

623-73-4

EDA

4-Chlorothiophenol Structure

106-54-7

4-Chlorothiophenol

~90%

Acetic acid,2-[(4-chlorophenyl)thio]-, ethyl ester Structure

52377-68-1

Acetic acid,2-[...

2-Naphthaldehyde Structure

66-99-9

2-Naphthaldehyde

Benzene, azido- Structure

622-37-7

Benzene, azido-

~90%

1-naphthalen-2-yl-N-phenylmethanimine Structure

18263-29-1

1-naphthalen-2-...

EDA Structure

623-73-4

EDA

Butanol Structure

71-36-3

Butanol

~88%

ethyl 2-butoxyacetate Structure

14144-70-8

ethyl 2-butoxya...


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