Organic letters

The power of solvent in altering the course of photorearrangements

P Sebej, BH Lim, BS Park, RS Givens, P Klán

Index: Sebej, Peter; Lim, Bum Hee; Park, Bong Ser; Givens, Richard S.; Klan, Petr Organic Letters, 2011 , vol. 13, # 4 p. 644 - 647

Full Text: HTML

Citation Number: 15

Abstract

A clean bifurcation between two important photochemical reactions through competition of a triplet state Type II H-abstraction reaction with a photo-Favorskii rearrangement for (o/p)- hydroxy-o-methylphenacyl esters that depends on the water content of the solvent has been established. The switch from the anhydrous Type II pathway that yields indanones to the aqueous-dependent pathway producing benzofuranones occurs abruptly at low water ...

 Related Synthetic Route
4′-Hydroxy-2′-methylacetophenone Structure

875-59-2

4′-Hydroxy-2′-m...

~%

5-(BENZYLOXY)-2,3-DIHYDRO-1H-INDEN-1-ONE Structure

78326-88-2

5-(BENZYLOXY)-2...

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2-(4-hydroxy-2-methylphenyl)-2-oxoethyl formate Structure

1265683-76-8

2-(4-hydroxy-2-...

~%

5-(BENZYLOXY)-2,3-DIHYDRO-1H-INDEN-1-ONE Structure

78326-88-2

5-(BENZYLOXY)-2...

Learn More
4-Benzyloxy-3-Methylacetophenone Structure

608119-82-0

4-Benzyloxy-3-M...

~%

5-(BENZYLOXY)-2,3-DIHYDRO-1H-INDEN-1-ONE Structure

78326-88-2

5-(BENZYLOXY)-2...

Learn More
2-bromo-1-(4-hydroxy-2-methylphenyl)-1-ethanone Structure

41877-16-1

2-bromo-1-(4-hy...

~%

5-(BENZYLOXY)-2,3-DIHYDRO-1H-INDEN-1-ONE Structure

78326-88-2

5-(BENZYLOXY)-2...

Learn More
Benzyl bromide Structure

100-39-0

Benzyl bromide

~%

5-(BENZYLOXY)-2,3-DIHYDRO-1H-INDEN-1-ONE Structure

78326-88-2

5-(BENZYLOXY)-2...

Learn More
N/A Structure

1265683-77-9

N/A

~%

5-(BENZYLOXY)-2,3-DIHYDRO-1H-INDEN-1-ONE Structure

78326-88-2

5-(BENZYLOXY)-2...

Learn More
diazomethane Structure

186581-53-3

diazomethane

4-Hydroxy-2-methylbenzoic acid Structure

578-39-2

4-Hydroxy-2-met...

~92%

methyl 4-hydroxy-2-methylbenzoate Structure

57556-31-7

methyl 4-hydrox...

Learn More
methyl 4-hydroxy-2-methylbenzoate Structure

57556-31-7

methyl 4-hydrox...

~67%

4-(hydroxymethyl)-3-methylphenol Structure

22574-58-9

4-(hydroxymethy...

Learn More
2-(4-hydroxy-2-methylphenyl)-2-oxoethyl formate Structure

1265683-76-8

2-(4-hydroxy-2-...

methyl iodide Structure

74-88-4

methyl iodide

~0%

4-(hydroxymethyl)-3-methylphenol Structure

22574-58-9

4-(hydroxymethy...

methyl 2-(4-hydroxy-2-methylphenyl)acetate Structure

114474-04-3

methyl 2-(4-hyd...

Learn More
2-bromo-1-(4-hydroxy-2-methylphenyl)-1-ethanone Structure

41877-16-1

2-bromo-1-(4-hy...

~%

4-(hydroxymethyl)-3-methylphenol Structure

22574-58-9

4-(hydroxymethy...

4-HYDROXY-2-METHYLPHENYLACETIC ACID Structure

29336-53-6

4-HYDROXY-2-MET...

Learn More
4′-Hydroxy-2′-methylacetophenone Structure

875-59-2

4′-Hydroxy-2′-m...

~%

4-(hydroxymethyl)-3-methylphenol Structure

22574-58-9

4-(hydroxymethy...

4-HYDROXY-2-METHYLPHENYLACETIC ACID Structure

29336-53-6

4-HYDROXY-2-MET...

Learn More
2-bromo-1-(4-hydroxy-2-methylphenyl)-1-ethanone Structure

41877-16-1

2-bromo-1-(4-hy...

~%

4-(hydroxymethyl)-3-methylphenol Structure

22574-58-9

4-(hydroxymethy...

methyl 2-(4-hydroxy-2-methylphenyl)acetate Structure

114474-04-3

methyl 2-(4-hyd...

Learn More
4′-Hydroxy-2′-methylacetophenone Structure

875-59-2

4′-Hydroxy-2′-m...

~%

4-(hydroxymethyl)-3-methylphenol Structure

22574-58-9

4-(hydroxymethy...

methyl 2-(4-hydroxy-2-methylphenyl)acetate Structure

114474-04-3

methyl 2-(4-hyd...

Learn More
2-(4-hydroxy-2-methylphenyl)-2-oxoethyl methanesulfonate Structure

1265683-74-6

2-(4-hydroxy-2-...

~%

4-(hydroxymethyl)-3-methylphenol Structure

22574-58-9

4-(hydroxymethy...

4-HYDROXY-2-METHYLPHENYLACETIC ACID Structure

29336-53-6

4-HYDROXY-2-MET...

Learn More
2-(4-hydroxy-2-methylphenyl)-2-oxoethyl acetate Structure

1265683-75-7

2-(4-hydroxy-2-...

~%

4-(hydroxymethyl)-3-methylphenol Structure

22574-58-9

4-(hydroxymethy...

4-HYDROXY-2-METHYLPHENYLACETIC ACID Structure

29336-53-6

4-HYDROXY-2-MET...

Learn More
N/A Structure

1265683-79-1

N/A

~59%

3(2H)-Benzofuranone,4,6-dimethyl Structure

20895-44-7

3(2H)-Benzofura...

5-Methyl-7-hydroxy-1-indanone Structure

68293-32-3

5-Methyl-7-hydr...

4,6-Dimethyl-2(3H)-benzofuranone Structure

33901-25-6

4,6-Dimethyl-2(...

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

16108-50-2

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

~%

3(2H)-Benzofuranone,4,6-dimethyl Structure

20895-44-7

3(2H)-Benzofura...

5-Methyl-7-hydroxy-1-indanone Structure

68293-32-3

5-Methyl-7-hydr...

4,6-Dimethyl-2(3H)-benzofuranone Structure

33901-25-6

4,6-Dimethyl-2(...

Learn More
2-benzyloxy-4,6-dimethylacetophenone Structure

1265683-72-4

2-benzyloxy-4,6...

~%

3(2H)-Benzofuranone,4,6-dimethyl Structure

20895-44-7

3(2H)-Benzofura...

5-Methyl-7-hydroxy-1-indanone Structure

68293-32-3

5-Methyl-7-hydr...

4,6-Dimethyl-2(3H)-benzofuranone Structure

33901-25-6

4,6-Dimethyl-2(...

Learn More
N/A Structure

1265683-81-5

N/A

~%

3(2H)-Benzofuranone,4,6-dimethyl Structure

20895-44-7

3(2H)-Benzofura...

5-Methyl-7-hydroxy-1-indanone Structure

68293-32-3

5-Methyl-7-hydr...

4,6-Dimethyl-2(3H)-benzofuranone Structure

33901-25-6

4,6-Dimethyl-2(...

Learn More
N/A Structure

1265683-82-6

N/A

~%

3(2H)-Benzofuranone,4,6-dimethyl Structure

20895-44-7

3(2H)-Benzofura...

5-Methyl-7-hydroxy-1-indanone Structure

68293-32-3

5-Methyl-7-hydr...

4,6-Dimethyl-2(3H)-benzofuranone Structure

33901-25-6

4,6-Dimethyl-2(...

Learn More
Phenol, 3,5-dimethyl-, 1-acetate Structure

877-82-7

Phenol, 3,5-dim...

~%

3(2H)-Benzofuranone,4,6-dimethyl Structure

20895-44-7

3(2H)-Benzofura...

5-Methyl-7-hydroxy-1-indanone Structure

68293-32-3

5-Methyl-7-hydr...

4,6-Dimethyl-2(3H)-benzofuranone Structure

33901-25-6

4,6-Dimethyl-2(...

Learn More
3,5-Dimethylphenol Structure

108-68-9

3,5-Dimethylphenol

~%

3(2H)-Benzofuranone,4,6-dimethyl Structure

20895-44-7

3(2H)-Benzofura...

5-Methyl-7-hydroxy-1-indanone Structure

68293-32-3

5-Methyl-7-hydr...

4,6-Dimethyl-2(3H)-benzofuranone Structure

33901-25-6

4,6-Dimethyl-2(...

Learn More

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