e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

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 ...

4′-Hydroxy-2′-methylacetophenone Structure

4′-Hydroxy-2′-m...

~%

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

5-(BENZYLOXY)-2...

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

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

~%

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

5-(BENZYLOXY)-2...

4-Benzyloxy-3-Methylacetophenone Structure

4-Benzyloxy-3-M...

~%

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

5-(BENZYLOXY)-2...

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

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

~%

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

5-(BENZYLOXY)-2...

Benzyl bromide Structure

~%

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

5-(BENZYLOXY)-2...

N/A Structure

~%

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

5-(BENZYLOXY)-2...

diazomethane Structure

4-Hydroxy-2-methylbenzoic acid Structure

4-Hydroxy-2-met...

~92%

methyl 4-hydroxy-2-methylbenzoate Structure

methyl 4-hydrox...

methyl 4-hydroxy-2-methylbenzoate Structure

methyl 4-hydrox...

~67%

4-(hydroxymethyl)-3-methylphenol Structure

4-(hydroxymethy...

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

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

methyl iodide Structure

~0%

4-(hydroxymethyl)-3-methylphenol Structure

4-(hydroxymethy...

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

methyl 2-(4-hyd...

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

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

~%

4-(hydroxymethyl)-3-methylphenol Structure

4-(hydroxymethy...

4-HYDROXY-2-METHYLPHENYLACETIC ACID Structure

4-HYDROXY-2-MET...

4′-Hydroxy-2′-methylacetophenone Structure

4′-Hydroxy-2′-m...

~%

4-(hydroxymethyl)-3-methylphenol Structure

4-(hydroxymethy...

4-HYDROXY-2-METHYLPHENYLACETIC ACID Structure

4-HYDROXY-2-MET...

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

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

~%

4-(hydroxymethyl)-3-methylphenol Structure

4-(hydroxymethy...

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

methyl 2-(4-hyd...

4′-Hydroxy-2′-methylacetophenone Structure

4′-Hydroxy-2′-m...

~%

4-(hydroxymethyl)-3-methylphenol Structure

4-(hydroxymethy...

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

methyl 2-(4-hyd...

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

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

~%

4-(hydroxymethyl)-3-methylphenol Structure

4-(hydroxymethy...

4-HYDROXY-2-METHYLPHENYLACETIC ACID Structure

4-HYDROXY-2-MET...

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

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

~%

4-(hydroxymethyl)-3-methylphenol Structure

4-(hydroxymethy...

4-HYDROXY-2-METHYLPHENYLACETIC ACID Structure

4-HYDROXY-2-MET...

N/A Structure

~59%

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

3(2H)-Benzofura...

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

5-Methyl-7-hydr...

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

4,6-Dimethyl-2(...

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

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

~%

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

3(2H)-Benzofura...

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

5-Methyl-7-hydr...

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

4,6-Dimethyl-2(...

2-benzyloxy-4,6-dimethylacetophenone Structure

2-benzyloxy-4,6...

~%

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

3(2H)-Benzofura...

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

5-Methyl-7-hydr...

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

4,6-Dimethyl-2(...

N/A Structure

~%

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

3(2H)-Benzofura...

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

5-Methyl-7-hydr...

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

4,6-Dimethyl-2(...

N/A Structure

~%

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

3(2H)-Benzofura...

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

5-Methyl-7-hydr...

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

4,6-Dimethyl-2(...

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

Phenol, 3,5-dim...

~%

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

3(2H)-Benzofura...

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

5-Methyl-7-hydr...

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

4,6-Dimethyl-2(...

3,5-Dimethylphenol Structure

3,5-Dimethylphenol

~%

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

3(2H)-Benzofura...

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

5-Methyl-7-hydr...

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

4,6-Dimethyl-2(...

Synthesis and inhibition study of monoamine oxidase, indolea...

[Reniers; Meinguet; Moineaux; Masereel; Vincent; Frederick; Wouters European Journal of Medicinal Chemistry, 2011 , vol. 46, # 12 p. 6104 - 6111]

Hydroxy-1-aminoindans and derivatives: Preparation, stabilit...

[Herzig, Yaacov; Lerman, Lena; Goldenberg, Willy; Lerner, David; Gottlieb, Hugo E.; Nudelman, Abraham Journal of Organic Chemistry, 2006 , vol. 71, # 11 p. 4130 - 4140]