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

Chemistry of quinone derivatives. Quinone monoketals via hydrolysis of electrochemically derived quinone bisketals

…, K Anderson, MJ Manning, JS Swenton

Index: Henton, Daniel R.; Anderson, Keith; Manning, Michael J.; Swenton, John S. Journal of Organic Chemistry, 1980 , vol. 45, # 17 p. 3422 - 3433

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Citation Number: 76

Abstract

The monohydrolysis of nine naphthoquinone bisketals and nine benzoquinone bisketals has been studied. In the acetamido, bromo, methyl, methoxy, and thiomethyl monosubstituted compounds, hydrolysis occurs at the ketal more distant from the substituent. The regiochemistry is nearly exclusive in the naphthoquinone series and is highly selective in the benzoquinone series. For disubstituted benzoquinone and ...

2,5-dimethoxytoluene Structure

2,5-dimethoxytoluene

Sodium Methylate Structure

Sodium Methylate

~%

3,3,6,6-tetramethoxy-1-methylcyclohexa-1,4-diene Structure

3,3,6,6-tetrame...

1,2,4-Trimethoxybenzene Structure

1,2,4-Trimethox...

Sodium Methylate Structure

Sodium Methylate

~2%

Benzene,1,2,4,5-tetramethoxy- Structure

Benzene,1,2,4,5...

3,4,4-Trimethoxy-2,5-cyclohexadien-1-one Structure

3,4,4-Trimethox...

Detail

1,1,4,4-Tetramethoxy-1,4-dihydronaphthalene Structure

1,1,4,4-Tetrame...

~90%

4,4-dimethoxynaphthalen-1-one Structure

4,4-dimethoxyna...

2-Bromo-1,1,4,4-tetramethoxy-1,4-dihydronaphthalene Structure

2-Bromo-1,1,4,4...

~%

4,4-dimethoxynaphthalen-1-one Structure

4,4-dimethoxyna...

1-bromo-3,3,6,6-tetramethoxycyclohexa-1,4-diene Structure

1-bromo-3,3,6,6...

~70%

2-Bromo-4-methoxyphenol Structure

2-Bromo-4-metho...

1-bromo-3,3,6,6-tetramethoxycyclohexa-1,4-diene Structure

1-bromo-3,3,6,6...

~2%

3-bromo-4,4-dimethoxycyclohexa-2,5-dien-1-one Structure

3-bromo-4,4-dim...

2-bromo-4,4-dimethoxycyclohexa-2,5-dien-1-one Structure

2-bromo-4,4-dim...

3,4,4-trimethoxynaphthalen-1-one Structure

3,4,4-trimethox...

~89%

3,4-dimethoxynaphthalen-1-ol Structure

3,4-dimethoxyna...

1,1,2,4,4-Pentamethoxy-1,4-dihydronaphthalene Structure

1,1,2,4,4-Penta...

~%

3,4-dimethoxynaphthalen-1-ol Structure

3,4-dimethoxyna...

1-bromo-3,3,6,6-tetramethoxycyclohexa-1,4-diene Structure

1-bromo-3,3,6,6...

~89%

3-bromo-4,4-dimethoxycyclohexa-2,5-dien-1-one Structure

3-bromo-4,4-dim...

2-bromo-4,4-dimethoxycyclohexa-2,5-dien-1-one Structure

2-bromo-4,4-dim...

3,3,6,6-tetramethoxy-1-methylcyclohexa-1,4-diene Structure

3,3,6,6-tetrame...

~65%

4,4-dimethoxy-3-methylcyclohexa-2,5-dien-1-one Structure

4,4-dimethoxy-3...

4,4-dimethoxy-2-methylcyclohexa-2,5-dienone Structure

4,4-dimethoxy-2...

1,1,2,4,4-Pentamethoxy-1,4-dihydronaphthalene Structure

1,1,2,4,4-Penta...

~27%

3,4,4-trimethoxynaphthalen-1-one Structure

3,4,4-trimethox...

1,1,4-trimethoxynaphthalen-2(1H)-one Structure

1,1,4-trimethox...

1,1,4-trimethoxynaphthalen-2(1H)-one Structure

1,1,4-trimethox...

~84%

1,4-dimethoxynaphthalen-2-ol Structure

1,4-dimethoxyna...

1,1,2,4,4-Pentamethoxy-1,4-dihydronaphthalene Structure

1,1,2,4,4-Penta...

~%

1,4-dimethoxynaphthalen-2-ol Structure

1,4-dimethoxyna...

1,1,4,4-Tetramethoxy-1,4-dihydronaphthalene Structure

1,1,4,4-Tetrame...

~80%

4-Methoxy-1-naphthol Structure

4-Methoxy-1-naphthol

1,2,4-Trimethoxybenzene Structure

1,2,4-Trimethox...

Sodium Methylate Structure

Sodium Methylate

~0%

Benzene,1,2,4,5-tetramethoxy- Structure

Benzene,1,2,4,5...

3,4,4-Trimethoxy-2,5-cyclohexadien-1-one Structure

3,4,4-Trimethox...

Detail