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

Intramolecular ring closure reactions of cyclopropene derivatives as a method for synthesizing novel tricyclic ring compounds

A Padwa, WF Rieker, RJ Rosenthal

Index: Padwa, Albert; Rieker, William F.; Rosenthal, Robert J. Journal of Organic Chemistry, 1984 , vol. 49, p. 1353 - 1360

Full Text: HTML

Citation Number: 13

Abstract

Albert Padwa,* William F. Rieker, and Robert J. Rosenthal ... Department of Chemistry, Emory University, Atlanta, Georgia 30322 Received October 19, 1983 ... The thermal and photosensitized reactions of several 4-(methyldiphenylcyclopropenyl)-l-butenes have been studied. The thermolysis of these systems gave substituted tricycle[ 3.2.0.@+']heptanes in good yield. The formation of this ring system involves bond formation between the ir-bond and the cyclopropene ring ...

1-(2-methyl-1,3-diphenylcycloprop-2-en-1-yl)-2-prop-2-enylbenzene Structure

1-(2-methyl-1,3...

~55%

2,2'-dimethyl-3'-phenylspiro[1,2-dihydroindene-3,1'-indene] Structure

2,2'-dimethyl-3...

1-but-3-enyl-2-methyl-3-phenyl-2,3-dihydroinden-1-ol Structure

1-but-3-enyl-2-...

~89%

3-but-3-enyl-2-methyl-1-phenyl-1H-indene Structure

3-but-3-enyl-2-...

(1-but-3-enyl-2-methyl-3-phenylcycloprop-2-en-1-yl)benzene Structure

(1-but-3-enyl-2...

~5%

7-methyl-1,2-diphenyltricyclo[3.2.0.02,7]heptane Structure

7-methyl-1,2-di...

N/A Structure

1-but-3-enyl-2-methyl-3-phenyl-1H-indene Structure

1-but-3-enyl-2-...

Detail

(2SR,3RS)-2-methyl-3-phenyl-2,3-dihydro-1H-inden-1-one Structure

(2SR,3RS)-2-met...

~%

3-but-3-enyl-2-methyl-1-phenyl-1H-indene Structure

3-but-3-enyl-2-...

(1-but-3-enyl-2-methyl-3-phenylcycloprop-2-en-1-yl)benzene Structure

(1-but-3-enyl-2...

~4%

7-methyl-1,2-diphenyltricyclo[3.2.0.02,7]heptane Structure

7-methyl-1,2-di...

7-methyl-1,6-diphenylbicyclo[4.1.0]hept-3-ene Structure

7-methyl-1,6-di...

N/A Structure

Detail

3-but-3-enyl-2-methyl-1-phenyl-1H-indene Structure

3-but-3-enyl-2-...

~31%

1-but-3-enyl-2-methyl-3-phenyl-1H-indene Structure

1-but-3-enyl-2-...

1-but-3-enyl-2-methyl-3-phenyl-2,3-dihydroinden-1-ol Structure

1-but-3-enyl-2-...

~%

1-but-3-enyl-2-methyl-3-phenyl-1H-indene Structure

1-but-3-enyl-2-...

(1-but-3-enyl-2-methyl-3-phenylcycloprop-2-en-1-yl)benzene Structure

(1-but-3-enyl-2...

~5%

7-methyl-1,2-diphenyltricyclo[3.2.0.02,7]heptane Structure

7-methyl-1,2-di...

N/A Structure

1-but-3-enyl-2-methyl-3-phenyl-1H-indene Structure

1-but-3-enyl-2-...

Detail

(2SR,3RS)-2-methyl-3-phenyl-2,3-dihydro-1H-inden-1-one Structure

(2SR,3RS)-2-met...

~%

1-but-3-enyl-2-methyl-3-phenyl-1H-indene Structure

1-but-3-enyl-2-...

(1-but-3-enyl-2-methyl-3-phenylcycloprop-2-en-1-yl)benzene Structure

(1-but-3-enyl-2...

~6%

7-methyl-1,2-diphenyltricyclo[3.2.0.02,7]heptane Structure

7-methyl-1,2-di...

7-methyl-1,6-diphenylbicyclo[4.1.0]hept-3-ene Structure

7-methyl-1,6-di...

N/A Structure

Detail

(1-but-3-enyl-2-methyl-3-phenylcycloprop-2-en-1-yl)benzene Structure

(1-but-3-enyl-2...

~5%

7-methyl-1,2-diphenyltricyclo[3.2.0.02,7]heptane Structure

7-methyl-1,2-di...

7-methyl-1,6-diphenylbicyclo[4.1.0]hept-3-ene Structure

7-methyl-1,6-di...

N/A Structure

Detail

4-Brombut-1-en Structure

(2SR,3RS)-2-methyl-3-phenyl-2,3-dihydro-1H-inden-1-one Structure

(2SR,3RS)-2-met...

~%

1-but-3-enyl-2-methyl-3-phenyl-2,3-dihydroinden-1-ol Structure

1-but-3-enyl-2-...

4-Brombut-1-en Structure

1,2-diphenyl-3-methylcyclopropenylium perchlorate Structure

1,2-diphenyl-3-...

~73%

(3-but-3-enyl-3-methyl-2-phenylcyclopropen-1-yl)benzene Structure

(3-but-3-enyl-3...

(1-but-3-enyl-2-methyl-3-phenylcycloprop-2-en-1-yl)benzene Structure

(1-but-3-enyl-2...

(3-but-3-enyl-3-methyl-2-phenylcyclopropen-1-yl)benzene Structure

(3-but-3-enyl-3...

~7%

1-methyl-6,7-diphenylbicyclo[4.1.0]hept-3-ene Structure

1-methyl-6,7-di...

4-methyl-5,6-diphenylbicyclo[4.1.0]hept-4-ene Structure

4-methyl-5,6-di...

2-methyl-1,7-diphenyltricyclo-[3.2.0.02,7]heptane Structure

2-methyl-1,7-di...

Detail

2-Bromochlorobenzene Structure

2-Bromochlorobenzene

~%

1-(1-methyl-2,3-diphenylcycloprop-2-en-1-yl)-2-prop-2-enylbenzene Structure

1-(1-methyl-2,3...

1-ALLYL-2-CHLOROBENZENE Structure

1-ALLYL-2-CHLOR...

1,2-diphenyl-3-methylcyclopropenylium perchlorate Structure

1,2-diphenyl-3-...

~%

1-(1-methyl-2,3-diphenylcycloprop-2-en-1-yl)-2-prop-2-enylbenzene Structure

1-(1-methyl-2,3...

1-(2-methyl-1,3-diphenylcycloprop-2-en-1-yl)-2-prop-2-enylbenzene Structure

1-(2-methyl-1,3...

4-Brombut-1-en Structure

1,2-diphenyl-3-methylcyclopropenylium perchlorate Structure

1,2-diphenyl-3-...

~0%

(3-but-3-enyl-3-methyl-2-phenylcyclopropen-1-yl)benzene Structure

(3-but-3-enyl-3...

(1-but-3-enyl-2-methyl-3-phenylcycloprop-2-en-1-yl)benzene Structure

(1-but-3-enyl-2...

N/A Structure

~72%

1-ethenyl-4-methyl-2,3-diphenylnaphthalene Structure

1-ethenyl-4-met...

2-Bromochlorobenzene Structure

2-Bromochlorobenzene

~%

1-(2-methyl-1,3-diphenylcycloprop-2-en-1-yl)-2-prop-2-enylbenzene Structure

1-(2-methyl-1,3...

1-ALLYL-2-CHLOROBENZENE Structure

1-ALLYL-2-CHLOR...

1,2-diphenyl-3-methylcyclopropenylium perchlorate Structure

1,2-diphenyl-3-...

~%

1-(1-methyl-2,3-diphenylcycloprop-2-en-1-yl)-2-prop-2-enylbenzene Structure

1-(1-methyl-2,3...

1-(2-methyl-1,3-diphenylcycloprop-2-en-1-yl)-2-prop-2-enylbenzene Structure

1-(2-methyl-1,3...