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

Sterisch gehinderte Alkene, IV. Darstellung einiger Octamethylcycloalkylidencycloalkane und verwandter Verbindungen

…, B Ziegenhagen, M Hebold, I Hardtke…

Index: Krebs, Adolf; Rueger, Wolfgang; Ziegenhagen, Birgit; Hebold, Maren; Hardtke, Ingrid; et al. Chemische Berichte, 1984 , vol. 117, # 1 p. 277 - 309

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Citation Number: 0

Abstract

Abstract Mit Hilfe der Thiadiazolin-und Selenadiazolin-Methode wurden 16 neue überbrückte Derivate des Tetra-tert-butylethens vom Typ 4 dargestellt. Mit wachsender Ringgliederzahl nimmt die Spannung in 4 zu. Die Grenzen der erwähnten Synthesewege liegen für die Alkene bei 4m, n, p und q; sie stellen die Alkene höchster Fragmentierungsspannung dar, die bisher isoliert wurden. Die Ursachen für das ...

(2,2,4,4-tetramethylthietan-3-ylidene)hydrazine Structure

(2,2,4,4-tetram...

~50%

2,2,4,4-tetramethylthietane-3-thione Structure

2,2,4,4-tetrame...

1,1,3,3,7,7,12,12-Octamethyl-5-thia-13,14-diazadispiro<3.1.6.2>tetradec-13-en Structure

1,1,3,3,7,7,12,...

~45%

1,1,3,3,6,6,11,11-octamethyl-12-thiadispiro[3.0.65.14]dodecane Structure

1,1,3,3,6,6,11,...

(2,2,7,7-tetramethylcycloheptylidene)hydrazine Structure

(2,2,7,7-tetram...

~%

1,1,3,3,6,6,11,11-octamethyl-12-thiadispiro[3.0.65.14]dodecane Structure

1,1,3,3,6,6,11,...

N/A Structure

~%

1,1,3,3,6,6,11,11-octamethyl-12-thiadispiro[3.0.65.14]dodecane Structure

1,1,3,3,6,6,11,...

2,2,4,4-tetramethylcyclobutane-1-thione Structure

2,2,4,4-tetrame...

~%

1,1,3,3,6,6,11,11-octamethyl-12-thiadispiro[3.0.65.14]dodecane Structure

1,1,3,3,6,6,11,...

2-diazo-1,1,3,3-tetramethylcycloheptane Structure

2-diazo-1,1,3,3...

~%

1,1,3,3,6,6,11,11-octamethyl-12-thiadispiro[3.0.65.14]dodecane Structure

1,1,3,3,6,6,11,...

7,7-Di-tert-butyl-1,1,3,3-tetramethyl-8-thia-5,6-diazaspiro(3.4)oct-5-en Structure

7,7-Di-tert-but...

~61%

2,2-ditert-butyl-4,4,6,6-tetramethyl-1-thiaspiro[2.3]hexane Structure

2,2-ditert-buty...

1,1,3,3,6,6,8,8-octamethyl-9-thiadispiro[3.0.35.14]nonane Structure

1,1,3,3,6,6,8,8...

di-(tert-butyl)-Diazomethane Structure

di-(tert-butyl)...

~%

2,2-ditert-butyl-4,4,6,6-tetramethyl-1-thiaspiro[2.3]hexane Structure

2,2-ditert-buty...

2,2,4,4-tetramethylcyclobutane-1-thione Structure

2,2,4,4-tetrame...

~%

2,2-ditert-butyl-4,4,6,6-tetramethyl-1-thiaspiro[2.3]hexane Structure

2,2-ditert-buty...

1,1,3,3,6,6,8,8-octamethyl-2,7,9-trithiadispiro[3.0.35.14]nonane Structure

1,1,3,3,6,6,8,8...

~69%

2,2,4,4-tetramethyl-3-(2,2,4,4-tetramethylthietan-3-ylidene)thietane Structure

2,2,4,4-tetrame...

(2,2,4,4-tetramethylthietan-3-ylidene)hydrazine Structure

(2,2,4,4-tetram...

~%

2,2,4,4-tetramethyl-3-(2,2,4,4-tetramethylthietan-3-ylidene)thietane Structure

2,2,4,4-tetrame...

Tetrahydro-3,3,5,5-tetramethyl-4H-pyran-4-on-(triphenylphosphoranyliden)hydrazon Structure

Tetrahydro-3,3,...

~78%

3,3,5,5-tetramethyloxane-4-thione Structure

3,3,5,5-tetrame...

(3,3,5,5-tetramethyloxan-4-ylidene)hydrazine Structure

(3,3,5,5-tetram...

~%

3,3,5,5-tetramethyloxane-4-thione Structure

3,3,5,5-tetrame...

Tetrahydro-3,3,5,5-tetramethyl-4H-pyran-4-on-(triphenylphosphoranyliden)hydrazon Structure

Tetrahydro-3,3,...

~74%

4-diazo-3,3,5,5-tetramethyloxane Structure

4-diazo-3,3,5,5...

(3,3,5,5-tetramethyloxan-4-ylidene)hydrazine Structure

(3,3,5,5-tetram...

~%

4-diazo-3,3,5,5-tetramethyloxane Structure

4-diazo-3,3,5,5...

2,2,4,4-tetramethylthietane-3-thione Structure

2,2,4,4-tetrame...

~%

2,2,4,4-tetramethyl-3-(2,2,4,4-tetramethylthietan-3-ylidene)thietane Structure

2,2,4,4-tetrame...

7,7-Di-tert-butyl-1,1,3,3-tetramethyl-2,8-dithia-5,6-diazaspiro(3.4)oct-5-en Structure

7,7-Di-tert-but...

~%

2,2,4,4-tetramethyl-3-(2,2,4,4-tetramethylthietan-3-ylidene)thietane Structure

2,2,4,4-tetrame...

2,2,6,6-Tetramethylcyclohexanon-p-tolylsulfonylhydrazon Structure

2,2,6,6-Tetrame...

~89%

2-diazo-1,1,3,3-tetramethylcyclohexane Structure

2-diazo-1,1,3,3...

7,7-Di-tert-butyl-1,1,3,3-tetramethyl-2,8-dithia-5,6-diazaspiro(3.4)oct-5-en Structure

7,7-Di-tert-but...

~9%

2,2-Di-tert-butyl-4,4,6,6-tetramethyl-1,5-dithiaspiro<2.3>hexan Structure

2,2-Di-tert-but...

1,1,3,3,6,6,8,8-octamethyl-2,7,9-trithiadispiro[3.0.35.14]nonane Structure

1,1,3,3,6,6,8,8...

(2,2,4,4-tetramethylthietan-3-ylidene)hydrazine Structure

(2,2,4,4-tetram...

~%

1,1,3,3,6,6,8,8-octamethyl-2,7,9-trithiadispiro[3.0.35.14]nonane Structure

1,1,3,3,6,6,8,8...

2,2,4,4-tetramethylthietane-3-thione Structure

2,2,4,4-tetrame...

~%

1,1,3,3,6,6,8,8-octamethyl-2,7,9-trithiadispiro[3.0.35.14]nonane Structure

1,1,3,3,6,6,8,8...

3,3,6,6-tetramethyloxepane-4,5-dione Structure

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

~71%

4-hydroxy-3,3,5,5-tetramethyloxane-4-carboxylic acid Structure

4-hydroxy-3,3,5...

1,1,3,3,-Tetramethyl-2-indanselon-Radikalanion Structure

1,1,3,3,-Tetram...

~%

2-butylselanyl-1,1,3,3-tetramethyl-2H-indene Structure

2-butylselanyl-...

Tributylphosphine Structure

Tributylphosphine

1,1'',3,3''-Tetrahydro-1,1,1'',1'',3,3,3'',3''-octamethyldispiro[2H-inden-2,2'-[1,3,4]selenadiazol-5',2''-[2H]inden] Structure

1,1'',3,3''-Tet...

~8%

1,1',3,3'-Tetrahydro-1,1,1'1',3,3,3',3'-octamethyl-2,2'-bi-2H-indenyliden Structure

1,1',3,3'-Tetra...

2-butylselanyl-1,1,3,3-tetramethyl-2H-indene Structure

2-butylselanyl-...

1,1,5,5,9,9,13,13-Octamethyl-7-selena-3,11-dithia-14,15-diazadispiro(5.1.5.2)pentadec-14-en Structure

1,1,5,5,9,9,13,...

~68%

2,2,6-trimethyl-4-thiabicyclo[4.1.0]heptane Structure

2,2,6-trimethyl...

1-thia-3,3,5,5-tetramethylcyclohexane-4-selone Structure

1-thia-3,3,5,5-...

~%

2,2,6-trimethyl-4-thiabicyclo[4.1.0]heptane Structure

2,2,6-trimethyl...

1,1,3,3,6,6,8,8-octamethyl-9-thiadispiro[3.0.35.14]nonane Structure

1,1,3,3,6,6,8,8...

~80%

1,1,3,3-tetramethyl-2-(2,2,4,4-tetramethylcyclobutylidene)cyclobutane Structure

1,1,3,3-tetrame...

2,2,4,4-tetramethylcyclobutane-1-thione Structure

2,2,4,4-tetrame...

~%

1,1,3,3-tetramethyl-2-(2,2,4,4-tetramethylcyclobutylidene)cyclobutane Structure

1,1,3,3-tetrame...

2-diazo-1,1,3,3-tetramethylcyclobutane Structure

2-diazo-1,1,3,3...

~%

1,1,3,3-tetramethyl-2-(2,2,4,4-tetramethylcyclobutylidene)cyclobutane Structure

1,1,3,3-tetrame...

7,7-Di-tert-butyl-1,1,3,3-tetramethyl-8-thia-5,6-diazaspiro(3.4)oct-5-en Structure

7,7-Di-tert-but...

~%

1,1,3,3-tetramethyl-2-(2,2,4,4-tetramethylcyclobutylidene)cyclobutane Structure

1,1,3,3-tetrame...

1,1,3,3,7,7,9,9-Octamethyl-5-thia-10,11-diazadispiro(3.1.3.2)undec-10-en Structure

1,1,3,3,7,7,9,9...

~%

1,1,3,3-tetramethyl-2-(2,2,4,4-tetramethylcyclobutylidene)cyclobutane Structure

1,1,3,3-tetrame...

3,3,5,5-tetramethylthian-4-imine Structure

3,3,5,5-tetrame...

~74%

3,3,5,5-tetramethylthiane-4-thione Structure

3,3,5,5-tetrame...

3,3,5,5-Tetramethyl-1-thiacyclohexan-4-on Structure

3,3,5,5-Tetrame...

~%

3,3,5,5-tetramethylthiane-4-thione Structure

3,3,5,5-tetrame...

(2,2,7,7-tetramethylcycloheptylidene)hydrazine Structure

(2,2,7,7-tetram...

~10%

2-diazo-1,1,3,3-tetramethylcycloheptane Structure

2-diazo-1,1,3,3...

N/A Structure

~78%

2-diazo-1,1,3,3-tetramethylcycloheptane Structure

2-diazo-1,1,3,3...

2-diazo-1,1,3,3-tetramethylcyclohexane Structure

2-diazo-1,1,3,3...

~31%

2,2,6,6-tetramethylcyclohexane-1-thione Structure

2,2,6,6-tetrame...

2,2,6,6-Tetramethylcyclohexanon-p-tolylsulfonylhydrazon Structure

2,2,6,6-Tetrame...

~%

2,2,6,6-tetramethylcyclohexane-1-thione Structure

2,2,6,6-tetrame...

di-(tert-butyl)-Diazomethane Structure

di-(tert-butyl)...

~%

1,1,3,3-tetramethyl-2-(2,2,4,4-tetramethylcyclobutylidene)cyclobutane Structure

1,1,3,3-tetrame...

1,1,3,3-tetramethyl-2-indanone triphenyl-phosphoranylidenehydrazone Structure

1,1,3,3-tetrame...

~70%

2-diazo-1,1,3,3-tetramethylindene Structure

2-diazo-1,1,3,3...

7,7-Di-tert-butyl-1,1,3,3-tetramethyl-8-thia-5,6-diazaspiro(3.4)oct-5-en Structure

7,7-Di-tert-but...

~6%

2,2-ditert-butyl-4,4,6,6-tetramethyl-1-thiaspiro[2.3]hexane Structure

2,2-ditert-buty...

1,1,3,3,6,6,8,8-octamethyl-9-thiadispiro[3.0.35.14]nonane Structure

1,1,3,3,6,6,8,8...

1,1,3,3,7,7,9,9-Octamethyl-5-thia-10,11-diazadispiro(3.1.3.2)undec-10-en Structure

1,1,3,3,7,7,9,9...

~62%

1,1,3,3,6,6,8,8-octamethyl-9-thiadispiro[3.0.35.14]nonane Structure

1,1,3,3,6,6,8,8...

2,2,4,4-tetramethylcyclobutane-1-thione Structure

2,2,4,4-tetrame...

~%

1,1,3,3,6,6,8,8-octamethyl-9-thiadispiro[3.0.35.14]nonane Structure

1,1,3,3,6,6,8,8...

di-(tert-butyl)-Diazomethane Structure

di-(tert-butyl)...

~%

1,1,3,3,6,6,8,8-octamethyl-9-thiadispiro[3.0.35.14]nonane Structure

1,1,3,3,6,6,8,8...

2-diazo-1,1,3,3-tetramethylcyclobutane Structure

2-diazo-1,1,3,3...

~%

1,1,3,3,6,6,8,8-octamethyl-9-thiadispiro[3.0.35.14]nonane Structure

1,1,3,3,6,6,8,8...

1,1,3,3,7,7,10,10-Octamethyl-5-thia-8,9,11,12-tetraazadispiro(3.1.4.2)dodeca-8,11-dien Structure

1,1,3,3,7,7,10,...

~78%

1,1,3,3,6,6,9,9-octamethyl-10-thia-7,8-diazadispiro[3.0.45.14]dec-7-ene Structure

1,1,3,3,6,6,9,9...

2,2,4,4-tetramethylcyclobutane-1-thione Structure

2,2,4,4-tetrame...

~%

1,1,3,3,6,6,9,9-octamethyl-10-thia-7,8-diazadispiro[3.0.45.14]dec-7-ene Structure

1,1,3,3,6,6,9,9...

4-diazo-3,3,5,5-tetramethylpyrazole Structure

4-diazo-3,3,5,5...

~%

1,1,3,3,6,6,9,9-octamethyl-10-thia-7,8-diazadispiro[3.0.45.14]dec-7-ene Structure

1,1,3,3,6,6,9,9...

4-hydroxy-3,3,5,5-tetramethyloxane-4-carboxylic acid Structure

4-hydroxy-3,3,5...

~74%

3,3,5,5-tetramethyloxan-4-one Structure

3,3,5,5-tetrame...

3,3,6,6-tetramethyloxepane-4,5-dione Structure

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

~%

3,3,5,5-tetramethyloxan-4-one Structure

3,3,5,5-tetrame...

3,3,5,5-Tetramethyl-1-thiacyclohexan-4-on Structure

3,3,5,5-Tetrame...

~65%

3,3,5,5-tetramethylthian-4-imine Structure

3,3,5,5-tetrame...

1,1,3,3,7,7,10,10-Octamethyl-5-thia-11,12-diazadispiro(3.1.4.2)dodec-11-en Structure

1,1,3,3,7,7,10,...

~85%

1,1,3,3,6,6,9,9-octamethyl-10-thiadispiro[3.0.45.14]decane Structure

1,1,3,3,6,6,9,9...

2,2,5,5-Tetramethylcyclopentanon-p-tolylsulfonylhydrazon Structure

2,2,5,5-Tetrame...

~%

1,1,3,3,6,6,9,9-octamethyl-10-thiadispiro[3.0.45.14]decane Structure

1,1,3,3,6,6,9,9...

2,2,4,4-tetramethylcyclobutane-1-thione Structure

2,2,4,4-tetrame...

~%

1,1,3,3,6,6,9,9-octamethyl-10-thiadispiro[3.0.45.14]decane Structure

1,1,3,3,6,6,9,9...

2-diazo-1,1,3,3-tetramethylcyclopentane Structure

2-diazo-1,1,3,3...

~%

1,1,3,3,6,6,9,9-octamethyl-10-thiadispiro[3.0.45.14]decane Structure

1,1,3,3,6,6,9,9...

1,1,3,3,7,7,11,11,-Octamethyl-9-oxa-5-thia-12,13-diazadispiro<3.1.5.2>tridec-12-en Structure

1,1,3,3,7,7,11,...

~38%

1,1,3,3,6,6,10,10-octamethyl-8-oxa-11-thiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

(3,3,5,5-tetramethyloxan-4-ylidene)hydrazine Structure

(3,3,5,5-tetram...

~%

1,1,3,3,6,6,10,10-octamethyl-8-oxa-11-thiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

2,2,4,4-tetramethylcyclobutane-1-thione Structure

2,2,4,4-tetrame...

~%

1,1,3,3,6,6,10,10-octamethyl-8-oxa-11-thiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

4-diazo-3,3,5,5-tetramethyloxane Structure

4-diazo-3,3,5,5...

~%

1,1,3,3,6,6,10,10-octamethyl-8-oxa-11-thiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

Tetrahydro-3,3,5,5-tetramethyl-4H-pyran-4-on-(triphenylphosphoranyliden)hydrazon Structure

Tetrahydro-3,3,...

~%

1,1,3,3,6,6,10,10-octamethyl-8-oxa-11-thiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

2,2,5,5-Tetramethylcyclopentanon-p-tolylsulfonylhydrazon Structure

2,2,5,5-Tetrame...

~65%

2-diazo-1,1,3,3-tetramethylcyclopentane Structure

2-diazo-1,1,3,3...

1,1,3,3,7,7,11,11-Octamethyl-5-thia-12,13-diazadispiro(3.1.5.2)tridec-12-en Structure

1,1,3,3,7,7,11,...

~66%

1,1,3,3,6,6,10,10-octamethyl-11-thiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

2,2,6,6-Tetramethylcyclohexanon-p-tolylsulfonylhydrazon Structure

2,2,6,6-Tetrame...

~%

1,1,3,3,6,6,10,10-octamethyl-11-thiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

2,2,4,4-tetramethylcyclobutane-1-thione Structure

2,2,4,4-tetrame...

~%

1,1,3,3,6,6,10,10-octamethyl-11-thiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

2-diazo-1,1,3,3-tetramethylcyclohexane Structure

2-diazo-1,1,3,3...

~%

1,1,3,3,6,6,10,10-octamethyl-11-thiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

2,2,4,4-tetramethylcyclobutane-1-thione Structure

2,2,4,4-tetrame...

~%

1,1,3,3,6,6,10,10-octamethyl-8,11-dithiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

4-diazo-3,3,5,5-tetramethyl-thiacyclohexane Structure

4-diazo-3,3,5,5...

~%

1,1,3,3,6,6,10,10-octamethyl-8,11-dithiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

1,1,3,3,7,7,11,11-Octamethyl-5,9-dithia-12,13-diazadispiro<3.1.5.2>tridec-12-en Structure

1,1,3,3,7,7,11,...

~24%

1,1,3,3,6,6,10,10-octamethyl-8,11-dithiadispiro[3.0.55.14]undecane Structure

1,1,3,3,6,6,10,...

Tetrahydro-3,3,5,5-tetramethyl-4-(2,2,4,4-tetramethylcyclobutyliden)-2H-thiopyran Structure

Tetrahydro-3,3,...

1,1,4,4,8,8,11,11-octamethyl-6-thia-12,13-diazadispiro[4.1.47.25]tridec-12-ene Structure

1,1,4,4,8,8,11,...

~80%

1,1,4,4,7,7,10,10-octamethyl-11-thiadispiro[4.0.46.15]undecane Structure

1,1,4,4,7,7,10,...

2,2,5,5-Tetramethylcyclopentanon-p-tolylsulfonylhydrazon Structure

2,2,5,5-Tetrame...

~%

1,1,4,4,7,7,10,10-octamethyl-11-thiadispiro[4.0.46.15]undecane Structure

1,1,4,4,7,7,10,...

2,2,6,6-Tetramethylcyclohexanon-p-tolylsulfonylhydrazon Structure

2,2,6,6-Tetrame...

~%

1,1,4,4,7,7,10,10-octamethyl-11-thiadispiro[4.0.46.15]undecane Structure

1,1,4,4,7,7,10,...

2-diazo-1,1,3,3-tetramethylcyclohexane Structure

2-diazo-1,1,3,3...

~%

1,1,4,4,7,7,10,10-octamethyl-11-thiadispiro[4.0.46.15]undecane Structure

1,1,4,4,7,7,10,...

2,2,5,5-tetramethylcyclopentanethione Structure

2,2,5,5-tetrame...

~%

1,1,4,4,7,7,10,10-octamethyl-11-thiadispiro[4.0.46.15]undecane Structure

1,1,4,4,7,7,10,...

2-diazo-1,1,3,3-tetramethylcyclopentane Structure

2-diazo-1,1,3,3...

~%

1,1,4,4,7,7,10,10-octamethyl-11-thiadispiro[4.0.46.15]undecane Structure

1,1,4,4,7,7,10,...

1,1,4,4,8,8,12,12-Octamethyl-6-thia-13,14-diazadispiro(4.1.5.2)tetradec-13-en Structure

1,1,4,4,8,8,12,...

~%

1,1,4,4,7,7,10,10-octamethyl-11-thiadispiro[4.0.46.15]undecane Structure

1,1,4,4,7,7,10,...

(2,2,5,5-Tetramethylcyclopentyl)-(2,2,6-trimethylbicyclo<4.1.0>hept-1-yl)sulfid Structure

(2,2,5,5-Tetram...

(2,2,6,6-Tetramethylcyclohexyl)-(2,2,5-trimethylbicyclo<3.1.0>hex-1-yl)-sulfid Structure

(2,2,6,6-Tetram...