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

1, 3??Dipolare Cycloadditionen, 90. Diphenylnitrilimin und substituierte Butadiene; Substituenteneffekte und Geschwindigkeit der Cycloaddition

…, R Huisgen, W Kolbeck, V Weberndörfer

Index: Fliege, Werner; Huisgen, Rolf; Kolbeck, Winfried; Weberndoerfer, Volkmar Chemische Berichte, 1983 , vol. 116, # 10 p. 3438 - 3460

Full Text: HTML

Citation Number: 6

Abstract

Abstract 1-Substituierte Butadiene nehmen Diphenylnitrilimin (2) nicht an der 1, 2-, sondern nur an der 3, 4-Doppelbindung auf; aus der regiospezifischen Cycloaddition gehen 5- substituierte 1, 3-Diphenyl-2-pyrazoline hervor. In den relativen Additionsgeschwindigkeiten , in Konkurrenzversuchen gemessen, kommt die von sterischen Faktoren befreite, elektronische Fernwirkung des trans-1-Substituenten zur Geltung. Im Einklang mit dem ...

2,5-diphenyl-3-(1-phenylethenyl)-3,4-dihydropyrazole Structure

2,5-diphenyl-3-...

~68%

1,3-diphenyl-5-(1-phenylethenyl)pyrazole Structure

1,3-diphenyl-5-...

(E)-1,3-diphenyl-5-(prop-1-en-1-yl)-1H-pyrazole Structure

(E)-1,3-dipheny...

~77%

2,5-DIPHENYL-2H-PYRAZOLE-3-CARBOXYLIC ACID Structure

2,5-DIPHENYL-2H...

1,3-diphenyl-5-[(E)-2-phenylethenyl]-1H-pyrazole Structure

1,3-diphenyl-5-...

~84%

2,5-DIPHENYL-2H-PYRAZOLE-3-CARBOXYLIC ACID Structure

2,5-DIPHENYL-2H...

3-(2,5-diphenylpyrazol-3-yl)prop-2-enenitrile Structure

3-(2,5-diphenyl...

~66%

2,5-DIPHENYL-2H-PYRAZOLE-3-CARBOXYLIC ACID Structure

2,5-DIPHENYL-2H...

methyl 3-(2,5-diphenylpyrazol-3-yl)prop-2-enoate Structure

methyl 3-(2,5-d...

~68%

2,5-DIPHENYL-2H-PYRAZOLE-3-CARBOXYLIC ACID Structure

2,5-DIPHENYL-2H...

1,3-diphenyl-5-prop-1-en-2-ylpyrazole Structure

1,3-diphenyl-5-...

~20%

2,5-DIPHENYL-2H-PYRAZOLE-3-CARBOXYLIC ACID Structure

2,5-DIPHENYL-2H...

1,3-Butadiene,2-methoxy- Structure

1,3-Butadiene,2...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

~0%

5-ethenyl-1,3-diphenylpyrazole Structure

5-ethenyl-1,3-d...

3-(1-methoxyethenyl)-2,5-diphenyl-3,4-dihydropyrazole Structure

3-(1-methoxyeth...

1,3-Butadiene,2-methoxy- Structure

1,3-Butadiene,2...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

~%

5-ethenyl-1,3-diphenylpyrazole Structure

5-ethenyl-1,3-d...

2-ethoxybuta-1,3-diene Structure

2-ethoxybuta-1,...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

~%

5-ethenyl-1,3-diphenylpyrazole Structure

5-ethenyl-1,3-d...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

chloroprene Structure

~0%

5-ethenyl-1,3-diphenylpyrazole Structure

5-ethenyl-1,3-d...

3-(1-chloroethenyl)-2,5-diphenyl-3,4-dihydropyrazole Structure

3-(1-chloroethe...

2-ethoxybuta-1,3-diene Structure

2-ethoxybuta-1,...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

~0%

3-(1-ethoxyethenyl)-2,5-diphenyl-3,4-dihydropyrazole Structure

3-(1-ethoxyethe...

5-ethenyl-1,3-diphenylpyrazole Structure

5-ethenyl-1,3-d...

1,3-diphenyl-5-(1-phenylethenyl)pyrazole Structure

1,3-diphenyl-5-...

~50%

(2,5-diphenylpyrazol-3-yl)-phenylmethanone Structure

(2,5-diphenylpy...

2,5-diphenyl-3-(1-phenylethenyl)-3,4-dihydropyrazole Structure

2,5-diphenyl-3-...

~%

(2,5-diphenylpyrazol-3-yl)-phenylmethanone Structure

(2,5-diphenylpy...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

chloroprene Structure

~80%

5-ethenyl-1,3-diphenylpyrazole Structure

5-ethenyl-1,3-d...

3-(1-chloroethenyl)-2,5-diphenyl-3,4-dihydropyrazole Structure

3-(1-chloroethe...

2-ethoxybuta-1,3-diene Structure

2-ethoxybuta-1,...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

~81%

3-(1-ethoxyethenyl)-2,5-diphenyl-3,4-dihydropyrazole Structure

3-(1-ethoxyethe...

5-ethenyl-1,3-diphenylpyrazole Structure

5-ethenyl-1,3-d...

trans-3-(1,3-Diphenyl-2-pyrazolin-5-yl)acrylsaeure-methylester Structure

trans-3-(1,3-Di...

~60%

methyl 3-(2,5-diphenylpyrazol-3-yl)prop-2-enoate Structure

methyl 3-(2,5-d...

3-(2,5-diphenyl-3,4-dihydropyrazol-3-yl)prop-2-enenitrile Structure

3-(2,5-diphenyl...

~94%

3-(2,5-diphenylpyrazol-3-yl)prop-2-enenitrile Structure

3-(2,5-diphenyl...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

isoprene Structure

~%

2,5-diphenyl-3-prop-1-en-2-yl-3,4-dihydropyrazole Structure

2,5-diphenyl-3-...

5-ethenyl-5-methyl-1,3-diphenyl-4H-pyrazole Structure

5-ethenyl-5-met...

1,3-Butadiene,2-methoxy- Structure

1,3-Butadiene,2...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

~73%

5-ethenyl-1,3-diphenylpyrazole Structure

5-ethenyl-1,3-d...

3-(1-methoxyethenyl)-2,5-diphenyl-3,4-dihydropyrazole Structure

3-(1-methoxyeth...

(Z)-2,4-pentadienenitrile Structure

(Z)-2,4-pentadi...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

~61%

3-(2,5-diphenyl-3,4-dihydropyrazol-3-yl)prop-2-enenitrile Structure

3-(2,5-diphenyl...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

isoprene Structure

~%

2,5-diphenyl-3-prop-1-en-2-yl-3,4-dihydropyrazole Structure

2,5-diphenyl-3-...

5-ethenyl-5-methyl-1,3-diphenyl-4H-pyrazole Structure

5-ethenyl-5-met...

buta-1,3-dien-2-ylbenzene Structure

buta-1,3-dien-2...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

~50%

5-ethenyl-1,3,5-triphenyl-4H-pyrazole Structure

5-ethenyl-1,3,5...

2,5-diphenyl-3-(1-phenylethenyl)-3,4-dihydropyrazole Structure

2,5-diphenyl-3-...

2,5-diphenyl-3-prop-1-en-2-yl-3,4-dihydropyrazole Structure

2,5-diphenyl-3-...

~%

1,3-diphenyl-5-prop-1-en-2-ylpyrazole Structure

1,3-diphenyl-5-...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

~%

1,3-diphenyl-5-prop-1-en-2-ylpyrazole Structure

1,3-diphenyl-5-...

isoprene Structure

~%

1,3-diphenyl-5-prop-1-en-2-ylpyrazole Structure

1,3-diphenyl-5-...

buta-1,3-dien-2-ylbenzene Structure

buta-1,3-dien-2...

N-Phenylbenzenecarbohydrazonoyl chloride Structure

N-Phenylbenzene...

~11%

5-ethenyl-1,3,5-triphenyl-4H-pyrazole Structure

5-ethenyl-1,3,5...

2,5-diphenyl-3-(1-phenylethenyl)-3,4-dihydropyrazole Structure

2,5-diphenyl-3-...