The Journal of Organic Chemistry

. alpha.-Alkoxyallylation of activated carbonyl compounds. A novel variant of the Michael reaction

RM Coates, SJ Hobbs

Index: Coates, Robert M.; Hobbs, Steven J. Journal of Organic Chemistry, 1984 , vol. 49, p. 140 - 152

Full Text: HTML

Citation Number: 32

Abstract

Enolic or readily enolizable carbonyl compounds undergo a-alkoxyallylation upon reaction with acetals of a,@-enals or ethoxyallene at temperatures ranging from 200 'C to ambient. Whereas reactions of the highly enolic or acidic carbonyl compounds (endocyclic 8- diketones, a-cyano ketones, a-nitro carbonyl compounds, and a-hydroxymethylene derivatives) occurred simply upon heating, alkylation of the less acidic exocyclic@- ...

 Related Synthetic Route
N/A Structure

23553-27-7

N/A

1H-Indene-1,3(2H)-dione,2-nitro- Structure

3674-33-7

1H-Indene-1,3(2...

~67%

2-(3-ethoxy-2-methylprop-2-enyl)-2-nitroindene-1,3-dione Structure

87698-35-9

2-(3-ethoxy-2-m...

1H-Indene-1,3(2H)-dione,2-nitro- Structure

3674-33-7

1H-Indene-1,3(2...

BENZENE, [1-(DIETHOXYMETHYL)ETHENYL]- Structure

80234-04-4

BENZENE, [1-(DI...

~40%

2-(3-ethoxy-2-phenylprop-2-enyl)-2-nitroindene-1,3-dione Structure

87698-36-0

2-(3-ethoxy-2-p...

ETHYL NITROACETATE Structure

626-35-7

ETHYL NITROACETATE

1-ethoxypropa-1,2-diene Structure

13077-71-9

1-ethoxypropa-1...

~26%

ethyl 5-ethoxy-2-nitropent-4-enoate Structure

87698-38-2

ethyl 5-ethoxy-...

ETHYL NITROACETATE Structure

626-35-7

ETHYL NITROACETATE

3,3-Diethoxy-1-propene Structure

3054-95-3

3,3-Diethoxy-1-...

~%

(Z)-Ethyl 5-ethoxy-2-nitro-4-pentenoate Structure

87698-39-3

(Z)-Ethyl 5-eth...

ethyl 5-ethoxy-2-nitropent-4-enoate Structure

87698-38-2

ethyl 5-ethoxy-...

3,3-Dimethoxy-1-propene Structure

6044-68-4

3,3-Dimethoxy-1...

methyl 2-cyano-3-hydroxyacrylate Structure

87698-54-2

methyl 2-cyano-...

~%

(Z)-Methyl 2-cyano-5-methoxy-4-pentenoate Structure

87698-43-9

(Z)-Methyl 2-cy...

methyl 2-cyano-5-methoxypent-4-enoate Structure

87698-42-8

methyl 2-cyano-...

3,3-Diethoxy-1-propene Structure

3054-95-3

3,3-Diethoxy-1-...

Dimedone Structure

126-81-8

Dimedone

~55%

2-ethoxy-7,7-dimethyl-3,4,6,8-tetrahydro-2H-chromen-5-one Structure

87698-48-4

2-ethoxy-7,7-di...

2-methyl-1,3-cyclohexandione Structure

1193-55-1

2-methyl-1,3-cy...

N/A Structure

23553-27-7

N/A

~54%

2-(3-ethoxy-2-methylprop-2-enyl)-2-methylcyclohexane-1,3-dione Structure

87698-50-8

2-(3-ethoxy-2-m...

2-Vinyl-1,3-dioxolane Structure

3984-22-3

2-Vinyl-1,3-dio...

2-methyl-1,3-cyclohexandione Structure

1193-55-1

2-methyl-1,3-cy...

~72%

2-[2-(1,3-dioxolan-2-yl)ethyl]-2-methylcyclohexane-1,3-dione Structure

87698-51-9

2-[2-(1,3-dioxo...

2-Vinyl-1,3-dioxolane Structure

3984-22-3

2-Vinyl-1,3-dio...

2-Oxocyclopentanecarbonitrile Structure

2941-29-9

2-Oxocyclopenta...

~52%

1-[2-(1,3-dioxolan-2-yl)ethyl]-2-oxocyclopentane-1-carbonitrile Structure

87698-52-0

1-[2-(1,3-dioxo...

Diethyl malonate Structure

105-53-3

Diethyl malonate

Ethyl formate Structure

109-94-4

Ethyl formate

~%

diethyl 2-(hydroxymethylidene)propanedioate Structure

20734-18-3

diethyl 2-(hydr...

3,3-Diethoxy-1-propene Structure

3054-95-3

3,3-Diethoxy-1-...

Ethyl acetoacetate Structure

141-97-9

Ethyl acetoacetate

~%

(Z)-Ethyl 2-acetyl-5-ethoxy-4-pentenoate Structure

87698-16-6

(Z)-Ethyl 2-ace...

ethyl 2-acetyl-5-ethoxypent-4-enoate Structure

87698-15-5

ethyl 2-acetyl-...

Ethyl (2E)-2-(ethoxymethylene)-3-oxobutanoate Structure

3788-94-1

Ethyl (2E)-2-(e...

~%

ethyl 2-acetyl-5-ethoxypent-4-enoate Structure

87698-15-5

ethyl 2-acetyl-...

3,3-Diethoxy-1-propene Structure

3054-95-3

3,3-Diethoxy-1-...

ethyl 2-(hydroxymethylidene)-3-oxobutanoate Structure

87698-53-1

ethyl 2-(hydrox...

~%

(Z)-Ethyl 2-acetyl-5-ethoxy-4-pentenoate Structure

87698-16-6

(Z)-Ethyl 2-ace...

ethyl 2-acetyl-5-ethoxypent-4-enoate Structure

87698-15-5

ethyl 2-acetyl-...

2-Vinyl-1,3-dioxolane Structure

3984-22-3

2-Vinyl-1,3-dio...

2-Methylcyclopentane-1,3-dione Structure

765-69-5

2-Methylcyclope...

~76%

2-[2-(1,3-dioxolan-2-yl)ethyl]-2-methylcyclopentane-1,3-dione Structure

87698-21-3

2-[2-(1,3-dioxo...

2-Methylcyclopentane-1,3-dione Structure

765-69-5

2-Methylcyclope...

3,3,3-triethoxyprop-1-ene Structure

42216-96-6

3,3,3-triethoxy...

~85%

2-methyl-2-(3,3,3-triethoxypropyl)cyclopentane-1,3-dione Structure

87698-22-4

2-methyl-2-(3,3...

Ethyl (2E)-2-(ethoxymethylene)-3-oxobutanoate Structure

3788-94-1

Ethyl (2E)-2-(e...

~%

ethyl 2-(hydroxymethylidene)-3-oxobutanoate Structure

87698-53-1

ethyl 2-(hydrox...

Methyl cyanoacetate Structure

105-34-0

Methyl cyanoacetate

Ethyl formate Structure

109-94-4

Ethyl formate

~51%

methyl 2-cyano-3-hydroxyacrylate Structure

87698-54-2

methyl 2-cyano-...

N/A Structure

23553-27-7

N/A

methyl 2-cyano-3-hydroxyacrylate Structure

87698-54-2

methyl 2-cyano-...

~86%

methyl 2-cyano-5-methoxy-4-methylpent-4-enoate Structure

87698-55-3

methyl 2-cyano-...

3,3-Diethoxy-1-propene Structure

3054-95-3

3,3-Diethoxy-1-...

Ethyl cyanoacetate Structure

105-56-6

Ethyl cyanoacetate

~%

(Z)-Ethyl 2-cyano-5-ethoxy-4-pentenoate Structure

87698-33-7

(Z)-Ethyl 2-cya...

ethyl 2-cyano-5-ethoxypent-4-enoate Structure

87698-32-6

ethyl 2-cyano-5...

N/A Structure

23553-27-7

N/A

2-Oxocyclopentanecarbonitrile Structure

2941-29-9

2-Oxocyclopenta...

~68%

1-(3-ethoxy-2-methylprop-2-enyl)-2-oxocyclopentane-1-carbonitrile Structure

87698-57-5

1-(3-ethoxy-2-m...

Dimethyl malonate Structure

108-59-8

Dimethyl malonate

Ethyl formate Structure

109-94-4

Ethyl formate

~%

dimethyl (hydroxymethylene)malonate Structure

27931-91-5

dimethyl (hydro...


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