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

Strained aromatic systems. Synthesis of cyclopropabenzocyclobutenes, cyclopropanaphthocylobutenes, and related compounds

D Davalian, PJ Garratt, W Koller…

Index: Davalian, Dariush; Garratt, Peter J.; Koller, Wolfgang; Mansuri, Muzammil M. Journal of Organic Chemistry, 1980 , vol. 45, # 21 p. 4183 - 4193

Full Text: HTML

Citation Number: 17

Abstract

The diene 9, prepared in four steps from diethyl cyclohex-4-ene-1, 2-dicarboxylate, was converted into cyclopropa [4, 5] benzocyclobutene (3) by photoirradiation to the cyclobutene 20 followed by treatment with KO-t-Bu and into cyclopropa [e] cyclobuta [blnaphthalene (45) by Diels-Alder addition to diethyl cyclobutene-1, 2-dicarboxylate, oxidation, and treatment with KO-t-Bu. Attempts to convert 9 into cyclopropa [b] anthracene were unsuccessful. The ...

N/A Structure

~92%

7,7-dichloro-3,4-dimethylidenebicyclo[4.1.0]heptane Structure

7,7-dichloro-3,...

(7,7-dichlorobicyclo[4.1.0]heptane-3,4-diyl)dimethyl bis(methanesulfonate) Structure

(7,7-dichlorobi...

~65%

7,7-dichloro-3,4-dimethylidenebicyclo[4.1.0]heptane Structure

7,7-dichloro-3,...

(1R,3R,4S,6S)-7,7-dichloro-3,4-bis(chloromethyl)bicyclo[4.1.0]heptane Structure

(1R,3R,4S,6S)-7...

~43%

7,7-dichloro-3,4-dimethylidenebicyclo[4.1.0]heptane Structure

7,7-dichloro-3,...

7,7-dichlorobicyclo[4.1.0]heptane-3,4-dimethanol Structure

7,7-dichlorobic...

~%

7,7-dichloro-3,4-dimethylidenebicyclo[4.1.0]heptane Structure

7,7-dichloro-3,...

7,7-dichloro-3,4-bis(carboethoxy)bicyclo-[4.1.0]heptane Structure

7,7-dichloro-3,...

~%

7,7-dichloro-3,4-dimethylidenebicyclo[4.1.0]heptane Structure

7,7-dichloro-3,...

7,7-dichlorobicyclo[4.1.0]hept-4-ene Structure

7,7-dichlorobic...

~39%

Bicyclo[4.1.0]hepta-1,3,5-triene Structure

Bicyclo[4.1.0]h...

cyclohexa-1,3-diene Structure

cyclohexa-1,3-diene

~%

Bicyclo[4.1.0]hepta-1,3,5-triene Structure

Bicyclo[4.1.0]h...

Naphtho[B]cyclopropene[E]cyclobutene Structure

Naphtho[B]cyclo...

~92%

5-iodo-6-(iodomethyl)-1,2-dihydrocyclobuta[b]naphthalene Structure

5-iodo-6-(iodom...

1,1-dichloro-1a,2,9,9a-tetrahydro-1H-cyclopropanthracene Structure

1,1-dichloro-1a...

potassium t-butoxide Structure

potassium t-butoxide

~40%

2-[(2-methylpropan-2-yl)oxymethyl]anthracene Structure

2-[(2-methylpro...

ctk2d6452 Structure

~61%

1,1-dichloro-1a,2,9,9a-tetrahydro-1H-cyclopropanthracene Structure

1,1-dichloro-1a...

4-Cyclohexene-1,2-dicarboxylicacid, 1,2-diethyl ester, (1R,2S)-rel- Structure

4-Cyclohexene-1...

~%

1,1-dichloro-1a,2,9,9a-tetrahydro-1H-cyclopropanthracene Structure

1,1-dichloro-1a...

7,7-dichlorobicyclo[4.1.0]heptane-3,4-dimethanol Structure

7,7-dichlorobic...

~%

1,1-dichloro-1a,2,9,9a-tetrahydro-1H-cyclopropanthracene Structure

1,1-dichloro-1a...

7,7-dichloro-3,4-bis(carboethoxy)bicyclo-[4.1.0]heptane Structure

7,7-dichloro-3,...

~%

1,1-dichloro-1a,2,9,9a-tetrahydro-1H-cyclopropanthracene Structure

1,1-dichloro-1a...

7,7-dichloro-3,4-dimethylidenebicyclo[4.1.0]heptane Structure

7,7-dichloro-3,...

~%

1,1-dichloro-1a,2,9,9a-tetrahydro-1H-cyclopropanthracene Structure

1,1-dichloro-1a...

N/A Structure

~%

1,1-dichloro-1a,2,9,9a-tetrahydro-1H-cyclopropanthracene Structure

1,1-dichloro-1a...

(1R,3R,4S,6S)-7,7-dichloro-3,4-bis(chloromethyl)bicyclo[4.1.0]heptane Structure

(1R,3R,4S,6S)-7...

~%

1,1-dichloro-1a,2,9,9a-tetrahydro-1H-cyclopropanthracene Structure

1,1-dichloro-1a...

(7,7-dichlorobicyclo[4.1.0]heptane-3,4-diyl)dimethyl bis(methanesulfonate) Structure

(7,7-dichlorobi...

~%

1,1-dichloro-1a,2,9,9a-tetrahydro-1H-cyclopropanthracene Structure

1,1-dichloro-1a...

benzene diazonium-2-carboxylate Structure

benzene diazoni...

7,7-dichloro-3,4-dimethylidenebicyclo[4.1.0]heptane Structure

7,7-dichloro-3,...

~58%

ctk2d6452 Structure

4-Cyclohexene-1,2-dicarboxylicacid, 1,2-diethyl ester, (1R,2S)-rel- Structure

4-Cyclohexene-1...

~%

ctk2d6452 Structure

7,7-dichlorobicyclo[4.1.0]heptane-3,4-dimethanol Structure

7,7-dichlorobic...

~%

ctk2d6452 Structure

7,7-dichloro-3,4-bis(carboethoxy)bicyclo-[4.1.0]heptane Structure

7,7-dichloro-3,...

~%

ctk2d6452 Structure

(1R,3R,4S,6S)-7,7-dichloro-3,4-bis(chloromethyl)bicyclo[4.1.0]heptane Structure

(1R,3R,4S,6S)-7...

~%

ctk2d6452 Structure

(7,7-dichlorobicyclo[4.1.0]heptane-3,4-diyl)dimethyl bis(methanesulfonate) Structure

(7,7-dichlorobi...

~%

ctk2d6452 Structure

N/A Structure

~%

ctk2d6452 Structure

1,2-Dihydrocyclobuta[a]cyclopropa[c]benzol Structure

1,2-Dihydrocycl...

~68%

4-(chloromethyl)bicyclo[4.2.0]octa-1(6),2,4-triene Structure

4-(chloromethyl...

3,4-Dihydro-1H-cyclobuta[a]cyclopropa[d]benzol Structure

3,4-Dihydro-1H-...

~79%

4-(chloromethyl)bicyclo[4.2.0]octa-1(6),2,4-triene Structure

4-(chloromethyl...

3-Cyclohexene-1,2-dicarboxylic acid dimethyl ester Structure

3-Cyclohexene-1...

~84%

[2-(hydroxymethyl)cyclohex-3-en-1-yl]methanol Structure

[2-(hydroxymeth...

1,1-dichloro-1a,2,9,9a-tetrahydro-1H-cyclopropanthracene Structure

1,1-dichloro-1a...

~39%

2-(chloromethyl)anthracene Structure

2-(chloromethyl...

1,2-Dihydrocyclobuta[a]cyclopropa[c]benzol Structure

1,2-Dihydrocycl...

~%

5-iodo-4-(iodomethyl)bicyclo[4.2.0]octa-1(6),2,4-triene Structure

5-iodo-4-(iodom...

3-iodo-2-(iodomethyl)bicyclo[4.2.0]octa-1,3,5-triene Structure

3-iodo-2-(iodom...

One pot synthesis of substituted tropones from 7, 7-dihalo-2...

[Kato; Yamamoto; Nomura; Miwa Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 1 p. 64 - 73]

Synthesis of Functionalized Cycloprop [f] indenes via the Ca...

[Mueller, Paul; Miao, Zhongshan Helvetica Chimica Acta, 1994 , vol. 77, p. 2051 - 2059]