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

Chemische Berichte

Carbanionisch induzierte [1, 3]??Wanderungen π??und koordinativ ungesättigter Gruppen

D Hellwinkel, F Lämmerzahl, G Hofmann

Index: Hellwinkel, Dieter; Laemmerzahl, Frank; Hofmann, Gunter Chemische Berichte, 1983 , vol. 116, # 10 p. 3375 - 3405

Full Text: HTML

Citation Number: 33

Abstract

Abstract Gemäß einem allgemeinen Reaktionsschema reagieren o-Lithioarylester 4a, b,- amide 13a, b, 17b und-amidine 39b von nicht enolisierbaren Carbonsäuren ebenso wie ein entsprechendes Diphenylphosphinsäureamid 51b unter milden Bedingungen zu den intensiv gefärbten Lithiumderivaten von o-Acylphenolen 6a, b und o-Acylarenaminen 15a, b, 18a, 41a, 52a, die abschließend zu den Neutralprodukten 7a, b, 14a, b, 18b, 41b, 52b ...

Benzamide, N-p-tolyl- Structure

Benzamide, N-p-...

~%

N-(2-bromo-4-methylphenyl)-N-methylbenzamide Structure

N-(2-bromo-4-me...

N-(2-Bromo-4-methylphenyl)benzamide Structure

N-(2-Bromo-4-me...

Dimethyl sulfate Structure

Dimethyl sulfate

~62%

N-(2-bromo-4-methylphenyl)-N-methylbenzamide Structure

N-(2-bromo-4-me...

2-Bromo-4-methylphenol Structure

2-Bromo-4-methy...

Benzoyl chloride Structure

Benzoyl chloride

~72%

benzoic acid,2-bromo-4-methylphenol Structure

benzoic acid,2-...

2-bromo-N-diphenylphosphoryl-N,4-dimethylaniline Structure

2-bromo-N-diphe...

~22%

2-diphenylphosphoryl-N,4-dimethylaniline Structure

2-diphenylphosp...

Acetamide,N-(2-bromo-4-methylphenyl)- Structure

Acetamide,N-(2-...

~%

2-diphenylphosphoryl-N,4-dimethylaniline Structure

2-diphenylphosp...

Chlorodiphenylphosphine Structure

Chlorodiphenylp...

~%

2-diphenylphosphoryl-N,4-dimethylaniline Structure

2-diphenylphosp...

N-(2-bromo-4-methylphenyl)-N-methylacetamide Structure

N-(2-bromo-4-me...

~%

2-diphenylphosphoryl-N,4-dimethylaniline Structure

2-diphenylphosp...

Diphenylphosphinic Chloride Structure

Diphenylphosphi...

~%

2-diphenylphosphoryl-N,4-dimethylaniline Structure

2-diphenylphosp...

di-p-tolylamine Structure

di-p-tolylamine

Pivaloyl chloride Structure

Pivaloyl chloride

~58%

2,2-dimethyl-N,N-bis(4-methylphenyl)propanamide Structure

2,2-dimethyl-N,...

(Z)-N,4-Dimethyl-2-((4-methylphenyl)(4-methylphenylimino)methyl)anilin Structure

(Z)-N,4-Dimethy...

~62%

p-Toluidine Structure

[5-methyl-2-(methylamino)phenyl]-(4-methylphenyl)methanone Structure

[5-methyl-2-(me...

2-Bromo-4-methylphenol Structure

2-Bromo-4-methy...

Pivaloyl chloride Structure

Pivaloyl chloride

~82%

(2-bromo-4-methylphenyl) 2,2-dimethylpropanoate Structure

(2-bromo-4-meth...

Pivaloyl chloride Structure

Pivaloyl chloride

~%

N-(2-bromo-4-methylphenyl)-2,2-dimethylpropanamide Structure

N-(2-bromo-4-me...

p-Toluidine Structure

~%

N-(2-bromo-4-methylphenyl)-2,2-dimethylpropanamide Structure

N-(2-bromo-4-me...

Acetamide,N-(2-bromo-4-methylphenyl)- Structure

Acetamide,N-(2-...

~%

2-bromo-N-(2,2-diphenylethenyl)-N,4-dimethylaniline Structure

2-bromo-N-(2,2-...

N-(2-bromo-4-methylphenyl)-N-methylacetamide Structure

N-(2-bromo-4-me...

~%

2-bromo-N-(2,2-diphenylethenyl)-N,4-dimethylaniline Structure

2-bromo-N-(2,2-...

Diphenylacetaldehyde Structure

Diphenylacetaldehyde

~%

N-(2,2-diphenylethenyl)-N,4-dimethylaniline Structure

N-(2,2-diphenyl...

Acetamide,N-(2-bromo-4-methylphenyl)- Structure

Acetamide,N-(2-...

~%

N-(2,2-diphenylethenyl)-N,4-dimethylaniline Structure

N-(2,2-diphenyl...

N-(2-bromo-4-methylphenyl)-N-methylacetamide Structure

N-(2-bromo-4-me...

~%

N-(2,2-diphenylethenyl)-N,4-dimethylaniline Structure

N-(2,2-diphenyl...

2-bromo-N-(2,2-diphenylethenyl)-N,4-dimethylaniline Structure

2-bromo-N-(2,2-...

~%

N-(2,2-diphenylethenyl)-N,4-dimethylaniline Structure

N-(2,2-diphenyl...

Benzamide, N-p-tolyl- Structure

Benzamide, N-p-...

~%

[5-methyl-2-(methylamino)phenyl]-phenylmethanone Structure

[5-methyl-2-(me...

N-(2-bromo-4-methylphenyl)-N-methylbenzamide Structure

N-(2-bromo-4-me...

~%

[5-methyl-2-(methylamino)phenyl]-phenylmethanone Structure

[5-methyl-2-(me...

N-(2-Bromo-4-methylphenyl)benzamide Structure

N-(2-Bromo-4-me...

~%

[5-methyl-2-(methylamino)phenyl]-phenylmethanone Structure

[5-methyl-2-(me...

2-Bromo-4-methylphenol Structure

2-Bromo-4-methy...

~%

(4-methylphenyl) 2,2-dimethylpropanoate Structure

(4-methylphenyl...

(2-bromo-4-methylphenyl) 2,2-dimethylpropanoate Structure

(2-bromo-4-meth...

~%

(4-methylphenyl) 2,2-dimethylpropanoate Structure

(4-methylphenyl...

2-Bromo-4-methylphenol Structure

2-Bromo-4-methy...

~%

1-(2-hydroxy-5-methylphenyl)-2,2-dimethylpropan-1-one Structure

1-(2-hydroxy-5-...

Pivaloyl chloride Structure

Pivaloyl chloride

~%

1-(2-hydroxy-5-methylphenyl)-2,2-dimethylpropan-1-one Structure

1-(2-hydroxy-5-...

(2-bromo-4-methylphenyl) 2,2-dimethylpropanoate Structure

(2-bromo-4-meth...

~%

p-Cresol Structure

1-(2-hydroxy-5-methylphenyl)-2,2-dimethylpropan-1-one Structure

1-(2-hydroxy-5-...

9-Aminophenanthrene Structure

9-Aminophenanthrene

Benzoyl chloride Structure

Benzoyl chloride

~41%

N-phenanthren-9-ylbenzamide Structure

N-phenanthren-9...

Acetamide,N-(2-bromo-4-methylphenyl)- Structure

Acetamide,N-(2-...

Dimethyl sulfate Structure

Dimethyl sulfate

~89%

N-(2-bromo-4-methylphenyl)-N-methylacetamide Structure

N-(2-bromo-4-me...

Propanamide,2,2-dimethyl-N-(4-methylphenyl)- Structure

Propanamide,2,2...

~%

N-(2-bromo-4-methylphenyl)-N,2,2-trimethylpropanamide Structure

N-(2-bromo-4-me...

Acetamide,N-(2-bromo-4-methylphenyl)- Structure

Acetamide,N-(2-...

~%

N-(2-bromo-4-methylphenyl)-N,2,2-trimethylpropanamide Structure

N-(2-bromo-4-me...

Pivaloyl chloride Structure

Pivaloyl chloride

~%

N-(2-bromo-4-methylphenyl)-N,2,2-trimethylpropanamide Structure

N-(2-bromo-4-me...

p-Toluidine Structure

~%

N-(2-bromo-4-methylphenyl)-N,2,2-trimethylpropanamide Structure

N-(2-bromo-4-me...

N-(2-bromo-4-methylphenyl)-N-methylacetamide Structure

N-(2-bromo-4-me...

~%

N-(2-bromo-4-methylphenyl)-N,2,2-trimethylpropanamide Structure

N-(2-bromo-4-me...

N-(2-bromo-4-methylphenyl)-2,2-dimethylpropanamide Structure

N-(2-bromo-4-me...

Dimethyl sulfate Structure

Dimethyl sulfate

~13%

N-(2-bromo-4-methylphenyl)-N,2,2-trimethylpropanamide Structure

N-(2-bromo-4-me...

Pivaloyl chloride Structure

Pivaloyl chloride

~%

2,2-dimethyl-1-[5-methyl-2-(methylamino)phenyl]propan-1-one Structure

2,2-dimethyl-1-...

Propanamide,2,2-dimethyl-N-(4-methylphenyl)- Structure

Propanamide,2,2...

~%

2,2-dimethyl-1-[5-methyl-2-(methylamino)phenyl]propan-1-one Structure

2,2-dimethyl-1-...

N-(2-bromo-4-methylphenyl)-N,2,2-trimethylpropanamide Structure

N-(2-bromo-4-me...

~%

2,2-dimethyl-1-[5-methyl-2-(methylamino)phenyl]propan-1-one Structure

2,2-dimethyl-1-...

N-(2-bromo-4-methylphenyl)-2,2-dimethylpropanamide Structure

N-(2-bromo-4-me...

~%

2,2-dimethyl-1-[5-methyl-2-(methylamino)phenyl]propan-1-one Structure

2,2-dimethyl-1-...

Acetamide,N-(2-bromo-4-methylphenyl)- Structure

Acetamide,N-(2-...

~%

2-Bromo-N,N,4-trimethylaniline Structure

2-Bromo-N,N,4-t...

N-(2-bromo-4-methylphenyl)-N-methylacetamide Structure

N-(2-bromo-4-me...

~%

2-Bromo-N,N,4-trimethylaniline Structure

2-Bromo-N,N,4-t...

N-(2-bromo-4-methylphenyl)-N-trimethylsilylbenzamide Structure

N-(2-bromo-4-me...

~27%

N-(2-Bromo-4-methylphenyl)benzamide Structure

N-(2-Bromo-4-me...

(2-AMINO-5-METHYLPHENYL)(PHENYL)METHANONE Structure

(2-AMINO-5-METH...

N-(4-methyl-2-trimethylsilylphenyl)benzamide Structure

N-(4-methyl-2-t...

N-phenanthren-9-ylbenzamide Structure

N-phenanthren-9...

~86%

N-(10-bromophenanthren-9-yl)benzamide Structure

N-(10-bromophen...

9-Aminophenanthrene Structure

9-Aminophenanthrene

~%

N-(10-bromophenanthren-9-yl)benzamide Structure

N-(10-bromophen...

Benzoyl chloride Structure

Benzoyl chloride

~%

N-(10-bromophenanthren-9-yl)benzamide Structure

N-(10-bromophen...

Tert-Butyllithium Structure

Tert-Butyllithium

N-(2-Brom-4-methylphenyl)-4-methyl-N-(4-methylphenylsulfonyl)benzamid Structure

N-(2-Brom-4-met...

~18%

N-(2-bromo-4-methylphenyl)-4-methylbenzenesulfonamide Structure

N-(2-bromo-4-me...

4-Methylbenzoic acid Structure

4-Methylbenzoic acid

Detail

N-(2-Brom-4-methylphenyl)-4-methyl-N-(4-methylphenylsulfonyl)benzamid Structure

N-(2-Brom-4-met...

~%

N-(2-bromo-4-methylphenyl)-4-methylbenzenesulfonamide Structure

N-(2-bromo-4-me...

4-Methylbenzoic acid Structure

4-Methylbenzoic acid

4-methyl-N-[4-methyl-2-(4-methylbenzoyl)phenyl]benzenesulfonamide Structure

4-methyl-N-[4-m...

Pivaloyl chloride Structure

Pivaloyl chloride

N-Methylaniline Structure

N-Methylaniline

~60%

N,2,2-trimethyl-N-phenylpropanamide Structure

N,2,2-trimethyl...

Tert-Butyllithium Structure

Tert-Butyllithium

N-(2-Brom-4-methylphenyl)-4-methyl-N-(4-methylphenylsulfonyl)benzamid Structure

N-(2-Brom-4-met...

~45%

N-(2-bromo-4-methylphenyl)-4-methylbenzenesulfonamide Structure

N-(2-bromo-4-me...

4-Methylbenzoic acid Structure

4-Methylbenzoic acid

Detail

N-(2-Brom-4-methylphenyl)-4-methyl-N-(4-methylphenylsulfonyl)benzamid Structure

N-(2-Brom-4-met...

~%

N-(2-bromo-4-methylphenyl)-4-methylbenzenesulfonamide Structure

N-(2-bromo-4-me...

4-Methylbenzoic acid Structure

4-Methylbenzoic acid

4-methyl-N-[4-methyl-2-(4-methylbenzoyl)phenyl]benzenesulfonamide Structure

4-methyl-N-[4-m...

Acetamide,N-(2-bromo-4-methylphenyl)- Structure

Acetamide,N-(2-...

~%

2-bromo-N,4-dimethyl-N-trimethylsilylaniline Structure

2-bromo-N,4-dim...

N-(2-bromo-4-methylphenyl)-N-methylacetamide Structure

N-(2-bromo-4-me...

~%

2-bromo-N,4-dimethyl-N-trimethylsilylaniline Structure

2-bromo-N,4-dim...

n-Butyllithium Structure

2-bromo-N,4-dimethyl-N-trimethylsilylaniline Structure

2-bromo-N,4-dim...

~16%

N-butyl-N,4-dimethyl-2-trimethylsilylaniline Structure

N-butyl-N,4-dim...

9-Aminophenanthrene Structure

9-Aminophenanthrene

~%

N-(10-bromophenanthren-9-yl)-N-methylbenzamide Structure

N-(10-bromophen...

N-phenanthren-9-ylbenzamide Structure

N-phenanthren-9...

~%

N-(10-bromophenanthren-9-yl)-N-methylbenzamide Structure

N-(10-bromophen...

Benzoyl chloride Structure

Benzoyl chloride

~%

N-(10-bromophenanthren-9-yl)-N-methylbenzamide Structure

N-(10-bromophen...

N-(10-bromophenanthren-9-yl)benzamide Structure

N-(10-bromophen...

Dimethyl sulfate Structure

Dimethyl sulfate

~69%

N-(10-bromophenanthren-9-yl)-N-methylbenzamide Structure

N-(10-bromophen...

9-Aminophenanthrene Structure

9-Aminophenanthrene

~%

[10-(methylamino)phenanthren-9-yl]-phenylmethanone Structure

[10-(methylamin...

N-phenanthren-9-ylbenzamide Structure

N-phenanthren-9...

~%

[10-(methylamino)phenanthren-9-yl]-phenylmethanone Structure

[10-(methylamin...

N-(10-bromophenanthren-9-yl)-N-methylbenzamide Structure

N-(10-bromophen...

~%

[10-(methylamino)phenanthren-9-yl]-phenylmethanone Structure

[10-(methylamin...

N-(10-bromophenanthren-9-yl)benzamide Structure

N-(10-bromophen...

~%

[10-(methylamino)phenanthren-9-yl]-phenylmethanone Structure

[10-(methylamin...

Chlorotrimethylsilane Structure

Chlorotrimethyl...

2-Bromo-N,N,4-trimethylaniline Structure

2-Bromo-N,N,4-t...

~64%

N,N,4-trimethyl-2-trimethylsilylaniline Structure

N,N,4-trimethyl...

METHYLLITHIUM Structure

2-bromo-N,4-dimethyl-N-trimethylsilylaniline Structure

2-bromo-N,4-dim...

~50%

N,N,4-trimethyl-2-trimethylsilylaniline Structure

N,N,4-trimethyl...

Acetamide,N-(2-bromo-4-methylphenyl)- Structure

Acetamide,N-(2-...

~%

N,N,4-trimethyl-2-trimethylsilylaniline Structure

N,N,4-trimethyl...

N-(2-bromo-4-methylphenyl)-N-methylacetamide Structure

N-(2-bromo-4-me...

~%

N,N,4-trimethyl-2-trimethylsilylaniline Structure

N,N,4-trimethyl...

Chlorotrimethylsilane Structure

Chlorotrimethyl...

N-(2-Bromo-4-methylphenyl)benzamide Structure

N-(2-Bromo-4-me...

~84%

N-(2-bromo-4-methylphenyl)-N-trimethylsilylbenzamide Structure

N-(2-bromo-4-me...

Benzamide, N-p-tolyl- Structure

Benzamide, N-p-...

~%

N-(2-bromo-4-methylphenyl)-N-trimethylsilylbenzamide Structure

N-(2-bromo-4-me...

benzoic acid,2-bromo-4-methylphenol Structure

benzoic acid,2-...

~%

Methanone,(2-hydroxy-5-methylphenyl)phenyl- Structure

Methanone,(2-hy...

benzoic acid Structure

N,N-bis(4-methylphenyl)benzamide Structure

N,N-bis(4-methy...

Tert-Butyllithium Structure

Tert-Butyllithium

~%

di-p-tolylamine Structure

di-p-tolylamine

4-tert-butyl-N,N-bis(4-methylphenyl)benzamide Structure

4-tert-butyl-N,...

Detail

N-(2-bromo-4-methylphenyl)-N-trimethylsilylbenzamide Structure

N-(2-bromo-4-me...

~30%

N-(2-Bromo-4-methylphenyl)benzamide Structure

N-(2-Bromo-4-me...

(2-AMINO-5-METHYLPHENYL)(PHENYL)METHANONE Structure

(2-AMINO-5-METH...

N-(4-methyl-2-trimethylsilylphenyl)benzamide Structure

N-(4-methyl-2-t...

Pivaloyl chloride Structure

Pivaloyl chloride

p-Toluidine Structure

~75%

Propanamide,2,2-dimethyl-N-(4-methylphenyl)- Structure

Propanamide,2,2...

di-p-tolylamine Structure

di-p-tolylamine

Benzoyl chloride Structure

Benzoyl chloride

~80%

N,N-bis(4-methylphenyl)benzamide Structure

N,N-bis(4-methy...

N,N-bis(4-methylphenyl)benzamide Structure

N,N-bis(4-methy...

Tert-Butyllithium Structure

Tert-Butyllithium

~%

di-p-tolylamine Structure

di-p-tolylamine

4-tert-butyl-N,N-bis(4-methylphenyl)benzamide Structure

4-tert-butyl-N,...

Detail

Chlorotrimethylsilane Structure

Chlorotrimethyl...

N-(2-Bromo-4-methylphenyl)benzamide Structure

N-(2-Bromo-4-me...

~47%

N-(4-methyl-2-trimethylsilylphenyl)benzamide Structure

N-(4-methyl-2-t...

N-(2-bromo-4-methylphenyl)-N-trimethylsilylbenzamide Structure

N-(2-bromo-4-me...

~32%

N-(2-Bromo-4-methylphenyl)benzamide Structure

N-(2-Bromo-4-me...

(2-AMINO-5-METHYLPHENYL)(PHENYL)METHANONE Structure

(2-AMINO-5-METH...

N-(4-methyl-2-trimethylsilylphenyl)benzamide Structure

N-(4-methyl-2-t...

Benzamide, N-p-tolyl- Structure

Benzamide, N-p-...

~%

N-(4-methyl-2-trimethylsilylphenyl)benzamide Structure

N-(4-methyl-2-t...

Acetamide,N-(2-bromo-4-methylphenyl)- Structure

Acetamide,N-(2-...

~%

2-bromo-N-diphenylphosphoryl-N,4-dimethylaniline Structure

2-bromo-N-diphe...

Chlorodiphenylphosphine Structure

Chlorodiphenylp...

~%

2-bromo-N-diphenylphosphoryl-N,4-dimethylaniline Structure

2-bromo-N-diphe...

N-(2-bromo-4-methylphenyl)-N-methylacetamide Structure

N-(2-bromo-4-me...

~%

2-bromo-N-diphenylphosphoryl-N,4-dimethylaniline Structure

2-bromo-N-diphe...

p-Toluidine Structure

p-toluoyl chloride Structure

p-toluoyl chloride

~96%

4-methyl-N-(4-methylphenyl)benzamide Structure

4-methyl-N-(4-m...

Pivaloyl chloride Structure

Pivaloyl chloride

~%

1-anilino-3,3-dimethylbutan-2-one Structure

1-anilino-3,3-d...

N-Methylaniline Structure

N-Methylaniline

~%

1-anilino-3,3-dimethylbutan-2-one Structure

1-anilino-3,3-d...

N,2,2-trimethyl-N-phenylpropanamide Structure

N,2,2-trimethyl...

~%

1-anilino-3,3-dimethylbutan-2-one Structure

1-anilino-3,3-d...

N-(3,3-dimethyl-2-oxobutyl)-2,2-dimethyl-N-phenylpropanamide Structure

N-(3,3-dimethyl...

Pivaloyl chloride Structure

Pivaloyl chloride

~%

N-(3,3-dimethyl-2-oxobutyl)-2,2-dimethyl-N-phenylpropanamide Structure

N-(3,3-dimethyl...

N-Methylaniline Structure

N-Methylaniline

~%

N-(3,3-dimethyl-2-oxobutyl)-2,2-dimethyl-N-phenylpropanamide Structure

N-(3,3-dimethyl...

N,2,2-trimethyl-N-phenylpropanamide Structure

N,2,2-trimethyl...

~%

1-anilino-3,3-dimethylbutan-2-one Structure

1-anilino-3,3-d...

N-(3,3-dimethyl-2-oxobutyl)-2,2-dimethyl-N-phenylpropanamide Structure

N-(3,3-dimethyl...