Tetrahedron

C-alkylation of β diketones with benzylpyridinium salts. Evidence for chain radical mechanisms

…, P Pacheco, M Prat, AR Katritzky, B Brycki

Index: Marquet, Jorge; Moreno-Manas, Marcial; Pacheco, Pedro; Prat, Maria; Katritzky, Alan R.; Brycki, Bogumil Tetrahedron, 1990 , vol. 46, # 15 p. 5333 - 5346

Full Text: HTML

Citation Number: 20

Abstract

1-(p-Substituted benzyl)-2, 4, 6-triphenylpyridinium cations react with β-diketone anions by mechanisms which depend on the para-substituent. The p-methoxybenzyl derivative undergoes SN1 displacement yielding O-and C-benzylated products. The pnitrobenzyl compound reacts by a chain radicaloid mechanism and gives high yields of C- pnitrobenzylated diketones. The parent benzyl compound forms some C-and some O- ...

 Related Synthetic Route
Benzyl bromide Structure

100-39-0

Benzyl bromide

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~15%

3-benzylpentane-2,4-dione Structure

1134-87-8

3-benzylpentane...

2,4-Pentanedione,3,3-bis(phenylmethyl)- Structure

53316-00-0

2,4-Pentanedion...

Detail
N-BENZYL-2,4,6-TRIPHENYL PYRIDINIUM TETRAFLUOROBORATE Structure

66310-10-9

N-BENZYL-2,4,6-...

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~40%

1-(2-Hydroxy-4,6-dimethylphenyl)ethanone Structure

16108-50-2

1-(2-Hydroxy-4,...

3-benzylpentane-2,4-dione Structure

1134-87-8

3-benzylpentane...

Detail
N-BENZYL-2,4,6-TRIPHENYL PYRIDINIUM TETRAFLUOROBORATE Structure

66310-10-9

N-BENZYL-2,4,6-...

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~29%

3-benzylpentane-2,4-dione Structure

1134-87-8

3-benzylpentane...

N/A Structure

130745-79-8

N/A

N-BENZYL-2,4,6-TRIPHENYL PYRIDINIUM TETRAFLUOROBORATE Structure

66310-10-9

N-BENZYL-2,4,6-...

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~41%

1-(2-Hydroxy-4,6-dimethylphenyl)ethanone Structure

16108-50-2

1-(2-Hydroxy-4,...

3-benzylpentane-2,4-dione Structure

1134-87-8

3-benzylpentane...

Detail
N-BENZYL-2,4,6-TRIPHENYL PYRIDINIUM TETRAFLUOROBORATE Structure

66310-10-9

N-BENZYL-2,4,6-...

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~19%

3-benzylpentane-2,4-dione Structure

1134-87-8

3-benzylpentane...

Bibenzyl Structure

103-29-7

Bibenzyl

Benzyl bromide Structure

100-39-0

Benzyl bromide

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~22%

3-benzylpentane-2,4-dione Structure

1134-87-8

3-benzylpentane...

2,4-Pentanedione,3,3-bis(phenylmethyl)- Structure

53316-00-0

2,4-Pentanedion...

Detail
N/A Structure

71017-85-1

N/A

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~58%

Bis(p-chlorophenyl)ethane Structure

5216-35-3

Bis(p-chlorophe...

3-(4-CHLOROBENZYL)-2,4-PENTANEDIONE Structure

61713-41-5

3-(4-CHLOROBENZ...

Detail
4-Chlorobenzyl bromide Structure

622-95-7

4-Chlorobenzyl ...

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~36%

3-(4-CHLOROBENZYL)-2,4-PENTANEDIONE Structure

61713-41-5

3-(4-CHLOROBENZ...

3,3-BIS(4-CHLOROBENZYL)-2,4-PENTANEDIONE Structure

130745-77-6

3,3-BIS(4-CHLOR...

N-BENZYL-2,4,6-TRIPHENYL PYRIDINIUM TETRAFLUOROBORATE Structure

66310-10-9

N-BENZYL-2,4,6-...

1,3-Diphenylpropane-1,3-dione Structure

120-46-7

1,3-Diphenylpro...

~26%

2-benzyl-1,3-diphenylpropane-1,3-dione Structure

28918-09-4

2-benzyl-1,3-di...

N/A Structure

130745-83-4

N/A

Detail
1-(4-nitro-benzyl)-2,4,6-triphenylpyridinium tetrafluoroborate Structure

83365-34-8

1-(4-nitro-benz...

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~62%

3-[(4-nitrophenyl)methyl]pentane-2,4-dione Structure

56699-21-9

3-[(4-nitrophen...

N/A Structure

115780-19-3

N/A

1-(4-nitro-benzyl)-2,4,6-triphenylpyridinium tetrafluoroborate Structure

83365-34-8

1-(4-nitro-benz...

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~6%

Benzene,1,1'-(1Z)-1,2-ethenediylbis[4-nitro- Structure

619-93-2

Benzene,1,1'-(1...

3-[(4-nitrophenyl)methyl]pentane-2,4-dione Structure

56699-21-9

3-[(4-nitrophen...

Detail
N-BENZYL-2,4,6-TRIPHENYL PYRIDINIUM TETRAFLUOROBORATE Structure

66310-10-9

N-BENZYL-2,4,6-...

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~12%

1-(2-Hydroxy-4,6-dimethylphenyl)ethanone Structure

16108-50-2

1-(2-Hydroxy-4,...

3-benzylpentane-2,4-dione Structure

1134-87-8

3-benzylpentane...

Detail
N-BENZYL-2,4,6-TRIPHENYL PYRIDINIUM TETRAFLUOROBORATE Structure

66310-10-9

N-BENZYL-2,4,6-...

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~12%

1-(2-Hydroxy-4,6-dimethylphenyl)ethanone Structure

16108-50-2

1-(2-Hydroxy-4,...

3-benzylpentane-2,4-dione Structure

1134-87-8

3-benzylpentane...

Detail
1-(4-methoxy-benzyl)-2,4,6-triphenylpyridinium tetrafluoroborate Structure

71017-75-9

1-(4-methoxy-be...

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~14%

N/A Structure

30881-24-4

N/A

1-methoxy-4-[(2-methylpropan-2-yl)oxymethyl]benzene Structure

56636-80-7

1-methoxy-4-[(2...

Detail
1-(4-methoxy-benzyl)-2,4,6-triphenylpyridinium tetrafluoroborate Structure

71017-75-9

1-(4-methoxy-be...

1,3-Diphenylpropane-1,3-dione Structure

120-46-7

1,3-Diphenylpro...

~24%

1-methoxy-4-[(2-methylpropan-2-yl)oxymethyl]benzene Structure

56636-80-7

1-methoxy-4-[(2...

2-(4-methoxybenzyl)-1,3-diphenylpropane-1,3-dione Structure

29045-01-0

2-(4-methoxyben...

Detail
1-(4-methoxy-benzyl)-2,4,6-triphenylpyridinium tetrafluoroborate Structure

71017-75-9

1-(4-methoxy-be...

1-Phenylbutane-1,3-dione Structure

93-91-4

1-Phenylbutane-...

~17%

1-methoxy-4-[(2-methylpropan-2-yl)oxymethyl]benzene Structure

56636-80-7

1-methoxy-4-[(2...

2-(4-methoxybenzyl)-1-phenylbutane-1,3-dione Structure

130745-72-1

2-(4-methoxyben...

Detail
N/A Structure

71017-85-1

N/A

2,4-Pentandione Structure

123-54-6

2,4-Pentandione

~6%

Bis(p-chlorophenyl)ethane Structure

5216-35-3

Bis(p-chlorophe...

3-(4-CHLOROBENZYL)-2,4-PENTANEDIONE Structure

61713-41-5

3-(4-CHLOROBENZ...

Detail
2,2,6,6-Tetramethylheptane-3,5-dione Structure

1118-71-4

2,2,6,6-Tetrame...

N/A Structure

71017-85-1

N/A

~13%

Bis(p-chlorophenyl)ethane Structure

5216-35-3

Bis(p-chlorophe...

p-chlorobenzylalcohol Structure

873-76-7

p-chlorobenzyla...

N/A Structure

71017-85-1

N/A

1-Phenylbutane-1,3-dione Structure

93-91-4

1-Phenylbutane-...

~6%

Bis(p-chlorophenyl)ethane Structure

5216-35-3

Bis(p-chlorophe...

N/A Structure

130745-73-2

N/A

Detail
N/A Structure

71017-85-1

N/A

1,3-Diphenylpropane-1,3-dione Structure

120-46-7

1,3-Diphenylpro...

~2%

Bis(p-chlorophenyl)ethane Structure

5216-35-3

Bis(p-chlorophe...

2-(4-chlorobenzyl)-1,3-diphenylpropane-1,3-dione Structure

130745-75-4

2-(4-chlorobenz...

Detail
N-BENZYL-2,4,6-TRIPHENYL PYRIDINIUM TETRAFLUOROBORATE Structure

66310-10-9

N-BENZYL-2,4,6-...

1-Phenylbutane-1,3-dione Structure

93-91-4

1-Phenylbutane-...

~20%

1,3-Butanedione,1-phenyl-2-(phenylmethyl)- Structure

28918-08-3

1,3-Butanedione...

N/A Structure

130745-82-3

N/A

Detail

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