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

Journal of the American Chemical Society

Dipole-stabilized carbanions: the. alpha.'lithiation of piperidides

P Beak, WJ Zajdel

Index: Beak, Peter; Zajdel, William J. Journal of the American Chemical Society, 1984 , vol. 106, # 4 p. 1010 - 1018

Full Text: HTML

Citation Number: 86

Abstract

Abstract: The a'lithiations and subsequent electrophilic substitutions of two series of piperidides are reported. In the cases of 2, 4, 6-triisopropylbenzopiperidide (5) and 4-tert- butyl-2, 4, 6-triisopropylbenzopiperidide (6) lithiations and electrophilic substitutions give a'- substituted products, as shown in Table I, which cannot be cleaved. 2, 2- Diethylbutanopiperidide (19), 4-phenyl-2, 2-diethylbutanopiperidide (20), and N, N-diethyl ...

2,4,6-TRIISOPROPYLBENZOIC ACID Structure

2,4,6-TRIISOPRO...

~%

(4-tert-butylpiperidin-1-yl)-[2,4,6-tri(propan-2-yl)phenyl]methanone Structure

(4-tert-butylpi...

4-tert-butylpiperidine Structure

4-tert-butylpip...

2,4,6-TRIISOPROPYLBENZOYL CHLORIDE Structure

2,4,6-TRIISOPRO...

~%

(4-tert-butylpiperidin-1-yl)-[2,4,6-tri(propan-2-yl)phenyl]methanone Structure

(4-tert-butylpi...

2,4,6-TRIISOPROPYLBENZOIC ACID Structure

2,4,6-TRIISOPRO...

~%

piperidin-1-yl-[2,4,6-tri(propan-2-yl)phenyl]methanone Structure

piperidin-1-yl-...

Piperidine Structure

2,4,6-TRIISOPROPYLBENZOYL CHLORIDE Structure

2,4,6-TRIISOPRO...

~%

piperidin-1-yl-[2,4,6-tri(propan-2-yl)phenyl]methanone Structure

piperidin-1-yl-...

Butanoic acid,2,2-diethyl- Structure

Butanoic acid,2...

~%

1-(2-butyl-4-phenylpiperidin-1-yl)-2,2-diethylbutan-1-one Structure

1-(2-butyl-4-ph...

Etzadroxil Structure

~%

1-(2-butyl-4-phenylpiperidin-1-yl)-2,2-diethylbutan-1-one Structure

1-(2-butyl-4-ph...

ETHYL 2,2-DIETHYLBUTYRATE Structure

ETHYL 2,2-DIETH...

~%

1-(2-butyl-4-phenylpiperidin-1-yl)-2,2-diethylbutan-1-one Structure

1-(2-butyl-4-ph...

Butyl iodide Structure

2,2-diethyl-1-(4-phenylpiperidin-1-yl)butan-1-one Structure

2,2-diethyl-1-(...

~%

1-(2-butyl-4-phenylpiperidin-1-yl)-2,2-diethylbutan-1-one Structure

1-(2-butyl-4-ph...

Butanoic acid,2,2-diethyl- Structure

Butanoic acid,2...

~%

2,2-diethyl-1-(4-phenylpiperidin-1-yl)butan-1-one Structure

2,2-diethyl-1-(...

Etzadroxil Structure

~%

2,2-diethyl-1-(4-phenylpiperidin-1-yl)butan-1-one Structure

2,2-diethyl-1-(...

ETHYL 2,2-DIETHYLBUTYRATE Structure

ETHYL 2,2-DIETH...

~%

2,2-diethyl-1-(4-phenylpiperidin-1-yl)butan-1-one Structure

2,2-diethyl-1-(...

N-dodecyl-N,2,2-triethylbutanamide Structure

N-dodecyl-N,2,2...

~77%

N-ethyltetradecan-2-amine Structure

N-ethyltetradec...

Butanoic acid,2,2-diethyl- Structure

Butanoic acid,2...

~%

N,2,2-triethyl-N-(1-hydroxy-1-phenylpropan-2-yl)butanamide Structure

N,2,2-triethyl-...

Etzadroxil Structure

~%

N,2,2-triethyl-N-(1-hydroxy-1-phenylpropan-2-yl)butanamide Structure

N,2,2-triethyl-...

ETHYL 2,2-DIETHYLBUTYRATE Structure

ETHYL 2,2-DIETH...

~%

N,2,2-triethyl-N-(1-hydroxy-1-phenylpropan-2-yl)butanamide Structure

N,2,2-triethyl-...

Benzaldehyde Structure

N,N,2,2-tetraethylbutanamide Structure

N,N,2,2-tetraet...

~%

N,2,2-triethyl-N-(1-hydroxy-1-phenylpropan-2-yl)butanamide Structure

N,2,2-triethyl-...

1-(2-butyl-4-phenylpiperidin-1-yl)-2,2-diethylbutan-1-one Structure

1-(2-butyl-4-ph...

~93%

2-butyl-4-phenylpiperidine Structure

2-butyl-4-pheny...

2,2-diethyl-1-(4-phenylpiperidin-1-yl)butan-1-one Structure

2,2-diethyl-1-(...

~%

2-butyl-4-phenylpiperidine Structure

2-butyl-4-pheny...

Etzadroxil Structure

~%

N-dodecyl-N,2,2-triethylbutanamide Structure

N-dodecyl-N,2,2...

ETHYL 2,2-DIETHYLBUTYRATE Structure

ETHYL 2,2-DIETH...

~%

N-dodecyl-N,2,2-triethylbutanamide Structure

N-dodecyl-N,2,2...

N,N,2,2-tetraethylbutanamide Structure

N,N,2,2-tetraet...

1-Bromododecane Structure

1-Bromododecane

~%

N-dodecyl-N,2,2-triethylbutanamide Structure

N-dodecyl-N,2,2...

2,4,6-TRIISOPROPYLBENZOIC ACID Structure

2,4,6-TRIISOPRO...

~%

N,N-diethyl-2,4,6-tri(propan-2-yl)benzamide Structure

N,N-diethyl-2,4...

2,4,6-TRIISOPROPYLBENZOYL CHLORIDE Structure

2,4,6-TRIISOPRO...

Diethylamine Structure

~%

N,N-diethyl-2,4,6-tri(propan-2-yl)benzamide Structure

N,N-diethyl-2,4...

Butanoic acid,2,2-diethyl- Structure

Butanoic acid,2...

~%

N,N,2,2-tetraethylbutanamide Structure

N,N,2,2-tetraet...

Etzadroxil Structure

~%

N,N,2,2-tetraethylbutanamide Structure

N,N,2,2-tetraet...

ETHYL 2,2-DIETHYLBUTYRATE Structure

ETHYL 2,2-DIETH...

~%

N,N,2,2-tetraethylbutanamide Structure

N,N,2,2-tetraet...

Butanoic acid,2,2-diethyl- Structure

Butanoic acid,2...

~%

N-dodecyl-N,2,2-triethylbutanamide Structure

N-dodecyl-N,2,2...

Etzadroxil Structure

Ethyl iodide Structure

~79%

ETHYL 2,2-DIETHYLBUTYRATE Structure

ETHYL 2,2-DIETH...

Butanoic acid,2,2-diethyl- Structure

Butanoic acid,2...

~%

2,2-diethyl-1-piperidin-1-ylbutan-1-one Structure

2,2-diethyl-1-p...

Etzadroxil Structure

~%

2,2-diethyl-1-piperidin-1-ylbutan-1-one Structure

2,2-diethyl-1-p...

ETHYL 2,2-DIETHYLBUTYRATE Structure

ETHYL 2,2-DIETH...

~%

2,2-diethyl-1-piperidin-1-ylbutan-1-one Structure

2,2-diethyl-1-p...

ETHYL 2,2-DIETHYLBUTYRATE Structure

ETHYL 2,2-DIETH...

~89%

Butanoic acid,2,2-diethyl- Structure

Butanoic acid,2...

Etzadroxil Structure

~%

Butanoic acid,2,2-diethyl- Structure

Butanoic acid,2...