β??Cleavage of Bis (homoallylic) Potassium Alkoxides. Two??Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar??Turmerone, α??Damascone, …

RL Snowden, SM Linder, BL Muller…

Index: Snowden, Roger L.; Linder, Simon M.; Muller, Bernard L.; Schulte, Karl H. Helvetica Chimica Acta, 1987 , vol. 70, p. 1858 - 1878

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Citation Number: 34

Abstract

Abstract The transformation of 36 bis (homoallylic) alcohols VII to alkenones IX and Xvia β- cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf. Scheme 2). These studies have established an order of β-cleavage for 2-propenyl, 1-methyl-2propenyl, 2-methyl-2-propenyl, 1, 1-dimethyl-2propenyl, and benzyl groups in alkoxides 49a–56a and have allowed a comparison between the β-cleavege reaction and the oxy-Cope ...

 Related Synthetic Route
methyl valerate Structure

624-24-8

methyl valerate

~%

oct-1-en-4-one Structure

65807-62-7

oct-1-en-4-one

Methyl 3-butenoate Structure

3724-55-8

Methyl 3-butenoate

ALLYL CHLORIDE Structure

107-05-1

ALLYL CHLORIDE

~75%

4-prop-2-enylhepta-1,6-dien-4-ol Structure

10202-75-2

4-prop-2-enylhe...

Methyl pivalate Structure

598-98-1

Methyl pivalate

ALLYL CHLORIDE Structure

107-05-1

ALLYL CHLORIDE

~86%

4-tert-butylhepta-1,6-dien-4-ol Structure

10202-74-1

4-tert-butylhep...

4-(2'-methylpropyl)-1,6-heptadien-4-ol Structure

71897-97-7

4-(2'-methylpro...

~%

6-methylhept-2-en-4-one Structure

49852-35-9

6-methylhept-2-...

6-methylhept-1-en-4-one Structure

54129-64-5

6-methylhept-1-...

Methyl isovalerate Structure

556-24-1

Methyl isovalerate

~%

6-methylhept-2-en-4-one Structure

49852-35-9

6-methylhept-2-...

methyl cyclogeranate Structure

28043-10-9

methyl cyclogeranate

~%

1,3,3-trimethylcyclohexene Structure

503-47-9

1,3,3-trimethyl...

4-benzyl-2,6-dimethyl-1,6-heptadien-4-ol Structure

81925-77-1

4-benzyl-2,6-di...

~%

Phorone Structure

504-20-1

Phorone

2,6-dimethyl-1,5-Heptadien-4-one Structure

5837-45-6

2,6-dimethyl-1,...

2,6-dimethyl-4-(2'-propenyl)-1,6-heptadien-4-ol Structure

81925-78-2

2,6-dimethyl-4-...

~0%

Phorone Structure

504-20-1

Phorone

6-methyl-hepta-1,5-dien-4-one Structure

33698-67-8

6-methyl-hepta-...

2,6-dimethyl-1,5-Heptadien-4-one Structure

5837-45-6

2,6-dimethyl-1,...

Detail
Methyl 3-methyl-2-butenoate Structure

924-50-5

Methyl 3-methyl...

~%

Phorone Structure

504-20-1

Phorone

3,3-Dimethylacrylic acid Structure

541-47-9

3,3-Dimethylacr...

~%

Phorone Structure

504-20-1

Phorone

N/A Structure

49815-59-0

N/A

~%

Damascone Structure

23726-91-2

Damascone

Damascone Structure

23726-92-3

Damascone

N/A Structure

31089-73-3

N/A

6,6-dimethyl-2-methyl-1-cyclohexene-1-carboxylic acid methyl ester Structure

49815-58-9

6,6-dimethyl-2-...

~%

Damascone Structure

23726-92-3

Damascone

methyl cyclogeranate Structure

28043-10-9

methyl cyclogeranate

~%

1,5,5-trimethylcyclohexene Structure

503-46-8

1,5,5-trimethyl...

2,6-dimethyl-4-(1'-methylpropyl)-1,6-heptadien-4-ol Structure

81925-74-8

2,6-dimethyl-4-...

~%

2,5-dimethylhept-2-en-4-one Structure

62939-80-4

2,5-dimethylhep...

2,5-dimethyl-hept-1-en-4-one Structure

81925-82-8

2,5-dimethyl-he...

Methyl 2-methylbutyrate Structure

868-57-5

Methyl 2-methyl...

~%

2,5-dimethylhept-2-en-4-one Structure

62939-80-4

2,5-dimethylhep...

2,6-Dimethyl-4-phenyl-1,6-heptadien-4-ol Structure

81925-76-0

2,6-Dimethyl-4-...

~%

Seneciophenone Structure

5650-07-7

Seneciophenone

3-methyl-1-phenylbut-3-en-1-one Structure

52813-35-1

3-methyl-1-phen...

2,6-Dimethyl-4-phenyl-1,6-heptadien-4-ol Structure

81925-76-0

2,6-Dimethyl-4-...

~%

Seneciophenone Structure

5650-07-7

Seneciophenone

3-methyl-1-phenylbut-3-en-1-one Structure

52813-35-1

3-methyl-1-phen...

N/A Structure

94853-53-9

N/A

~%

2-methyl-6-(4-methylphenyl)hept-1-en-4-one Structure

87173-82-8

2-methyl-6-(4-m...

4'-Methylacetophenone Structure

122-00-9

4'-Methylacetop...

~%

2-methyl-6-(4-methylphenyl)hept-1-en-4-one Structure

87173-82-8

2-methyl-6-(4-m...

(+/-)-ethyl 3-(4-methylphenyl)butanoate Structure

6090-00-2

(+/-)-ethyl 3-(...

~%

2-methyl-6-(4-methylphenyl)hept-1-en-4-one Structure

87173-82-8

2-methyl-6-(4-m...

2,6-dimethyl-4-(2'-(4''-methylphenyl)propyl)-1,6-diheptadien-4-ol Structure

87149-97-1

2,6-dimethyl-4-...

~%

ar-turmerone Structure

38142-58-4

ar-turmerone

2-methyl-6-(4-methylphenyl)hept-1-en-4-one Structure

87173-82-8

2-methyl-6-(4-m...

4-(2'-methylpropyl)-1,6-heptadien-4-ol Structure

71897-97-7

4-(2'-methylpro...

~%

6-methylhept-2-en-4-one Structure

49852-35-9

6-methylhept-2-...

6-methylhept-1-en-4-one Structure

54129-64-5

6-methylhept-1-...

Methyl isovalerate Structure

556-24-1

Methyl isovalerate

~%

6-methylhept-1-en-4-one Structure

54129-64-5

6-methylhept-1-...

Methyl isovalerate Structure

556-24-1

Methyl isovalerate

~%

2,6-dimethylhept-2-en-4-one Structure

16525-05-6

2,6-dimethylhep...

2,6-dimethyl-4-(2'-(4''-methylphenyl)propyl)-1,6-diheptadien-4-ol Structure

87149-97-1

2,6-dimethyl-4-...

~%

ar-turmerone Structure

38142-58-4

ar-turmerone

2,6-dimethyl-4-(2'-(4''-methylphenyl)propyl)-1,6-diheptadien-4-ol Structure

87149-97-1

2,6-dimethyl-4-...

~%

ar-turmerone Structure

38142-58-4

ar-turmerone

2-methyl-6-(4-methylphenyl)hept-1-en-4-one Structure

87173-82-8

2-methyl-6-(4-m...

4-tert-butylhepta-1,6-dien-4-ol Structure

10202-74-1

4-tert-butylhep...

~%

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

20971-19-1

2,2-Dimethyl-4-...

2,2-dimethylhex-5-en-3-one Structure

55532-07-5

2,2-dimethylhex...

Methyl pivalate Structure

598-98-1

Methyl pivalate

~%

2,2-dimethylhex-5-en-3-one Structure

55532-07-5

2,2-dimethylhex...


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