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

Photolysis of the ozonide derived from 1, 4-benzodioxins. Synthesis of labile o-benzoquinones

C Kashima, A Tomotake, Y Omote

Index: Kashima, Choji; Tomotake, Atsushi; Omote, Yoshimori Journal of Organic Chemistry, 1987 , vol. 52, # 25 p. 5616 - 5621

Full Text: HTML

Citation Number: 18

Abstract

By the photolysis of the ozonide derived from 1, 4-benzodioxins, o-benzoquinones were obtained in moderate yields independent of the stability of o-benzoquinone@ and of the substituent groups, except the nitro group. Through the mechanistic studiea, it was indicated that 0-benzoquinonea were formed through a radical decomposition pathway, while catechols were formed through an ionic decomposition pathway induced by acidic ...

3,5-Cyclohexadiene-1,2-dione, 4-(1,1-dimethylethyl)- Structure

3,5-Cyclohexadi...

~%

6-tert-butyl-1,4-benzodioxine Structure

6-tert-butyl-1,...

4-tert-Butylcatechol Structure

4-tert-Butylcatechol

~%

6-tert-butyl-1,4-benzodioxine Structure

6-tert-butyl-1,...

6-tert-butyl-2,3-dihydro-1,4-benzodioxine Structure

6-tert-butyl-2,...

~%

6-tert-butyl-1,4-benzodioxine Structure

6-tert-butyl-1,...

8-(tert-butyl)-2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

8-(tert-butyl)-...

~%

6-tert-butyl-1,4-benzodioxine Structure

6-tert-butyl-1,...

1,2-Benzenediol Structure

1,2-Benzenediol

~%

1,4-Benzodioxin Structure

1,4-Benzodioxin

2,5-dimethyl-2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

2,5-dimethyl-2,...

~%

1,4-Benzodioxin Structure

1,4-Benzodioxin

2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

2,5-epoxybenzo[...

~%

1,4-Benzodioxin Structure

1,4-Benzodioxin

6-benzoyl-1,4-benzodioxin Structure

6-benzoyl-1,4-b...

~92%

(3,4-Dihydroxyphenyl)(phenyl)methanone Structure

(3,4-Dihydroxyp...

2,5-dimethyl-2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

2,5-dimethyl-2,...

~%

1,4-Benzodioxan Structure

1,4-Benzodioxan

2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

2,5-epoxybenzo[...

~%

1,4-Benzodioxan Structure

1,4-Benzodioxan

8-(tert-butyl)-2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

8-(tert-butyl)-...

~%

4-T-BUTYL-5-METHOXY-O-BENZOQUINONE Structure

4-T-BUTYL-5-MET...

Methanol Structure

3,5-Cyclohexadiene-1,2-dione, 4-(1,1-dimethylethyl)- Structure

3,5-Cyclohexadi...

~24%

4-T-BUTYL-5-METHOXY-O-BENZOQUINONE Structure

4-T-BUTYL-5-MET...

4-tert-Butylcatechol Structure

4-tert-Butylcatechol

1,2-Benzenediol Structure

1,2-Benzenediol

~%

benzene-1,2-diol,formic acid Structure

benzene-1,2-dio...

2,5-dimethyl-2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

2,5-dimethyl-2,...

~%

benzene-1,2-diol,formic acid Structure

benzene-1,2-dio...

2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

2,5-epoxybenzo[...

~%

benzene-1,2-diol,formic acid Structure

benzene-1,2-dio...

1,4-Benzodioxan Structure

1,4-Benzodioxan

~%

benzene-1,2-diol,formic acid Structure

benzene-1,2-dio...

1,4-Benzodioxin Structure

1,4-Benzodioxin

~%

benzene-1,2-diol,formic acid Structure

benzene-1,2-dio...

1,2-Benzenediol Structure

1,2-Benzenediol

4-tert-Butylcatechol Structure

4-tert-Butylcatechol

1,2-Dibromoethane Structure

1,2-Dibromoethane

~%

6-tert-butyl-2,3-dihydro-1,4-benzodioxine Structure

6-tert-butyl-2,...

8-(tert-butyl)-2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

8-(tert-butyl)-...

~%

6-tert-butyl-2,3-dihydro-1,4-benzodioxine Structure

6-tert-butyl-2,...

3,5-Cyclohexadiene-1,2-dione, 4-(1,1-dimethylethyl)- Structure

3,5-Cyclohexadi...

~%

6-tert-butyl-2,3-dihydro-1,4-benzodioxine Structure

6-tert-butyl-2,...

3,5-Di-t-butylcatechol Structure

3,5-Di-t-butylc...

Benzyl triethylammonium chloride Structure

Benzyl triethyl...

~54%

4,6-ditert-butyl-1,3-benzodioxole Structure

4,6-ditert-buty...

5,7-ditert-butyl-1,4-benzodioxine Structure

5,7-ditert-buty...

7,9-di-tert-butyl-2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

7,9-di-tert-but...

~%

4,6-ditert-butyl-1,3-benzodioxole Structure

4,6-ditert-buty...

2,5-dimethyl-2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

2,5-dimethyl-2,...

~%

1,2-Benzenediol,1-acetate Structure

1,2-Benzenediol...

1,2-Benzenediol,1,2-diacetate Structure

1,2-Benzenediol...

1,2-Benzenediol Structure

1,2-Benzenediol

3,5-Di-t-butylcatechol Structure

3,5-Di-t-butylc...

Benzyl triethylammonium chloride Structure

Benzyl triethyl...

~41%

4,6-ditert-butyl-1,3-benzodioxole Structure

4,6-ditert-buty...

5,7-ditert-butyl-1,4-benzodioxine Structure

5,7-ditert-buty...

7,9-di-tert-butyl-2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

7,9-di-tert-but...

~%

5,7-ditert-butyl-1,4-benzodioxine Structure

5,7-ditert-buty...

8-(tert-butyl)-2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

8-(tert-butyl)-...

~22%

3,5-Cyclohexadiene-1,2-dione, 4-(1,1-dimethylethyl)- Structure

3,5-Cyclohexadi...

4-tert-Butylcatechol Structure

4-tert-Butylcatechol

7,9-di-tert-butyl-2,5-epoxybenzo[e][1,2,4,7]tetraoxocine Structure

7,9-di-tert-but...

~%

5,7-ditert-butyl-2,3-dihydro-1,4-benzodioxine Structure

5,7-ditert-buty...