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

Tetrahedron

Etude des petits cycles—XLII: Synthese des α-cyclopropylidene-cetones et aldehydes11Pour une publication préliminaire voir Ref. 1.

A Lechevallier, F Huet, JM Conia

Index: Lechevallier, A.; Huet, F.; Conia, J. M. Tetrahedron, 1983 , vol. 39, # 20 p. 3307 - 3316

Full Text: HTML

Citation Number: 13

Abstract

Cyclopropylidenation of α-keto-or α-formyl acetals by Witting reaction with cyclopropylidenetriphenyl-phosphorane leads to α cyclopropylidene-acetals, easily deacetalized by moist silicagel into the corresponding α-cyclopropylidene-ketone and α- cyclopropylidene-aldehydes. The conversion of the latter to the former is also easily carried out by reaction with Grignard reagents followed by oxidation with active manganese ...

1,1-Dimethoxyacetone Structure

1,1-Dimethoxyacetone

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

~%

1,1-dimethoxypropan-2-ylidenecyclopropane Structure

1,1-dimethoxypr...

2,2-dimethoxy phenylacetaldehyde Structure

2,2-dimethoxy p...

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

~%

(2-cyclopropylidene-1,1-dimethoxyethyl)benzene Structure

(2-cyclopropyli...

3,3-Diethoxy-2-butanone Structure

3,3-Diethoxy-2-...

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

~%

3,3-diethoxybutan-2-ylidenecyclopropane Structure

3,3-diethoxybut...

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

1-(2-methyl-1,3-dioxolan-2-yl)pentan-1-one Structure

1-(2-methyl-1,3...

~%

2-(1-cyclopropylidenepentyl)-2-methyl-1,3-dioxolane Structure

2-(1-cyclopropy...

2,2-diethoxypropanal Structure

2,2-diethoxypropanal

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

~%

2,2-diethoxypropylidenecyclopropane Structure

2,2-diethoxypro...

(2-cyclopropylidene-1,1-dimethoxyethyl)benzene Structure

(2-cyclopropyli...

~20%

2-cyclopropylidene-1-phenylethanone Structure

2-cyclopropylid...

1-(2-methoxy-2-phenylethenyl)cyclopropan-1-ol Structure

1-(2-methoxy-2-...

[1-methoxy-2-(1-methoxycyclopropyl)ethenyl]benzene Structure

[1-methoxy-2-(1...

Detail

(2-cyclopropylidene-1,1-dimethoxyethyl)benzene Structure

(2-cyclopropyli...

~20%

2-cyclopropylidene-1-phenylethanone Structure

2-cyclopropylid...

1-(2-methoxy-2-phenylethenyl)cyclopropan-1-ol Structure

1-(2-methoxy-2-...

[1-methoxy-2-(1-methoxycyclopropyl)ethenyl]benzene Structure

[1-methoxy-2-(1...

Detail

(2-cyclopropylidene-1,1-dimethoxyethyl)benzene Structure

(2-cyclopropyli...

~10%

2-cyclopropylidene-1-phenylethanone Structure

2-cyclopropylid...

1-(2-methoxy-2-phenylethenyl)cyclopropan-1-ol Structure

1-(2-methoxy-2-...

[1-methoxy-2-(1-methoxycyclopropyl)ethenyl]benzene Structure

[1-methoxy-2-(1...

Detail

(2-cyclopropylidene-1,1-dimethoxyethyl)benzene Structure

(2-cyclopropyli...

~9%

2-cyclopropylidene-1-phenylethanone Structure

2-cyclopropylid...

1-(2-methoxy-2-phenylethenyl)cyclopropan-1-ol Structure

1-(2-methoxy-2-...

[1-methoxy-2-(1-methoxycyclopropyl)ethenyl]benzene Structure

[1-methoxy-2-(1...

Detail

(2-cyclopropylidene-1,1-dimethoxyethyl)benzene Structure

(2-cyclopropyli...

~5%

2-cyclopropylidene-1-phenylethanone Structure

2-cyclopropylid...

1-(2-methoxy-2-phenylethenyl)cyclopropan-1-ol Structure

1-(2-methoxy-2-...

[1-methoxy-2-(1-methoxycyclopropyl)ethenyl]benzene Structure

[1-methoxy-2-(1...

Detail

2,2-diethoxypropylidenecyclopropane Structure

2,2-diethoxypro...

~86%

1-cyclopropylidenepropan-2-one Structure

1-cyclopropylid...

2-(1-cyclopropylidenepentyl)-2-methyl-1,3-dioxolane Structure

2-(1-cyclopropy...

~96%

3-cyclopropylideneheptan-2-one Structure

3-cyclopropylid...

1-(2-methyl-1,3-dioxolan-2-yl)pentan-1-one Structure

1-(2-methyl-1,3...

~%

3-cyclopropylideneheptan-2-one Structure

3-cyclopropylid...

2-methyl-1,3-dithiolane-2-carbaldehyde Structure

2-methyl-1,3-di...

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

~%

2-(cyclopropylidenemethyl)-2-methyl-1,3-dithiolane Structure

2-(cyclopropyli...

2,2-dimethoxycyclohexan-1-one Structure

2,2-dimethoxycy...

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

~%

2-cyclopropylidene-1,1-dimethoxycyclohexane Structure

2-cyclopropylid...

(2-cyclopropylidene-1,1-dimethoxyethyl)benzene Structure

(2-cyclopropyli...

~5%

2-cyclopropylidene-1-phenylethanone Structure

2-cyclopropylid...

1-(2-methoxy-2-phenylethenyl)cyclopropan-1-ol Structure

1-(2-methoxy-2-...

[1-methoxy-2-(1-methoxycyclopropyl)ethenyl]benzene Structure

[1-methoxy-2-(1...

Detail

2,2-diethoxyethylidenecyclopropane Structure

2,2-diethoxyeth...

~92%

2-cyclopropylideneacetaldehyde Structure

2-cyclopropylid...

N/A Structure

~49%

1-cyclopropyl-2-cyclopropylidenepropan-1-one Structure

1-cyclopropyl-2...

1,1-dimethoxypropan-2-ylidenecyclopropane Structure

1,1-dimethoxypr...

~%

1-cyclopropyl-2-cyclopropylidenepropan-1-one Structure

1-cyclopropyl-2...

2-cyclopropylidenepropanal Structure

2-cyclopropylid...

~%

1-cyclopropyl-2-cyclopropylidenepropan-1-one Structure

1-cyclopropyl-2...

cyclopropylidene-2 diphenyl-1,2 ethanol Structure

cyclopropyliden...

~56%

2-cyclopropylidene-1,2-diphenylethanone Structure

2-cyclopropylid...

cyclopropylidene-2 phenyl-2 ethanal Structure

cyclopropyliden...

~%

2-cyclopropylidene-1,2-diphenylethanone Structure

2-cyclopropylid...

Bromobenzene Structure

~%

2-cyclopropylidene-1,2-diphenylethanone Structure

2-cyclopropylid...

Ethanone,2,2-dimethoxy-1-phenyl- Structure

Ethanone,2,2-di...

~%

2-cyclopropylidene-1,2-diphenylethanone Structure

2-cyclopropylid...

(1-cyclopropylidene-2,2-dimethoxyethyl)benzene Structure

(1-cyclopropyli...

~%

2-cyclopropylidene-1,2-diphenylethanone Structure

2-cyclopropylid...

1,1-dimethoxypropan-2-ylidenecyclopropane Structure

1,1-dimethoxypr...

~99%

2-cyclopropylidenepropanal Structure

2-cyclopropylid...

cyclopropylidene-2 phenyl-1 propanol-1 Structure

cyclopropyliden...

~82%

2-cyclopropylidene-1-phenylpropan-1-one Structure

2-cyclopropylid...

2-cyclopropylidenepropanal Structure

2-cyclopropylid...

~%

2-cyclopropylidene-1-phenylpropan-1-one Structure

2-cyclopropylid...

1,1-dimethoxypropan-2-ylidenecyclopropane Structure

1,1-dimethoxypr...

~%

2-cyclopropylidene-1-phenylpropan-1-one Structure

2-cyclopropylid...

dicyclopropyl-1,2 cyclopropylidene-2 ethanol Structure

dicyclopropyl-1...

~50%

1,2-dicyclopropyl-2-cyclopropylideneethanone Structure

1,2-dicycloprop...

cyclopropyl-2 cyclopropylidene-2 ethanal Structure

cyclopropyl-2 c...

~%

1,2-dicyclopropyl-2-cyclopropylideneethanone Structure

1,2-dicycloprop...

1-cyclopropyl-2,2-dimethoxyethanone Structure

1-cyclopropyl-2...

~%

1,2-dicyclopropyl-2-cyclopropylideneethanone Structure

1,2-dicycloprop...

(1-cyclopropyl-2,2-dimethoxyethylidene)cyclopropane Structure

(1-cyclopropyl-...

~%

1,2-dicyclopropyl-2-cyclopropylideneethanone Structure

1,2-dicycloprop...

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

1-cyclopropyl-2,2-dimethoxyethanone Structure

1-cyclopropyl-2...

~%

(1-cyclopropyl-2,2-dimethoxyethylidene)cyclopropane Structure

(1-cyclopropyl-...

N-(2-furylmethyl)-2-nitro-benzamide Structure

N-(2-furylmethy...

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

~%

2,2-diethoxyethylidenecyclopropane Structure

2,2-diethoxyeth...

(2-cyclopropylidene-1,1-dimethoxyethyl)benzene Structure

(2-cyclopropyli...

~58%

2-cyclopropylidene-1-phenylethanone Structure

2-cyclopropylid...

1-(2-methoxy-2-phenylethenyl)cyclopropan-1-ol Structure

1-(2-methoxy-2-...

[1-methoxy-2-(1-methoxycyclopropyl)ethenyl]benzene Structure

[1-methoxy-2-(1...

Detail

(2-cyclopropylidene-1,1-dimethoxyethyl)benzene Structure

(2-cyclopropyli...

~59%

2-cyclopropylidene-1-phenylethanone Structure

2-cyclopropylid...

1-(2-methoxy-2-phenylethenyl)cyclopropan-1-ol Structure

1-(2-methoxy-2-...

[1-methoxy-2-(1-methoxycyclopropyl)ethenyl]benzene Structure

[1-methoxy-2-(1...

Detail

2,2-dimethoxy-1-phenylpropan-1-one Structure

2,2-dimethoxy-1...

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

~%

(1-cyclopropylidene-2,2-dimethoxypropyl)benzene Structure

(1-cyclopropyli...

2,2-dimethoxycyclopentan-1-one Structure

2,2-dimethoxycy...

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

~%

2-cyclopropylidene-1,1-dimethoxycyclopentane Structure

2-cyclopropylid...

(1-cyclopropylidene-2,2-dimethoxypropyl)benzene Structure

(1-cyclopropyli...

~89%

1-cyclopropylidene-1-phenylpropan-2-one Structure

1-cyclopropylid...

cyclopropylidene-1 phenyl-1 propanol-2 Structure

cyclopropyliden...

~34%

1-cyclopropylidene-1-phenylpropan-2-one Structure

1-cyclopropylid...

Ethanone,2,2-dimethoxy-1-phenyl- Structure

Ethanone,2,2-di...

~%

1-cyclopropylidene-1-phenylpropan-2-one Structure

1-cyclopropylid...

2,2-dimethoxy-1-phenylpropan-1-one Structure

2,2-dimethoxy-1...

~%

1-cyclopropylidene-1-phenylpropan-2-one Structure

1-cyclopropylid...

cyclopropylidene-2 phenyl-2 ethanal Structure

cyclopropyliden...

~%

1-cyclopropylidene-1-phenylpropan-2-one Structure

1-cyclopropylid...

(1-cyclopropylidene-2,2-dimethoxyethyl)benzene Structure

(1-cyclopropyli...

~%

1-cyclopropylidene-1-phenylpropan-2-one Structure

1-cyclopropylid...

2-cyclopropylidene-1,1-dimethoxycyclopentane Structure

2-cyclopropylid...

~62%

2-cyclopropylidenecyclopentan-1-one Structure

2-cyclopropylid...

2,2-dimethoxycyclopentan-1-one Structure

2,2-dimethoxycy...

~%

2-cyclopropylidenecyclopentan-1-one Structure

2-cyclopropylid...

Ethanone,2,2-dimethoxy-1-phenyl- Structure

Ethanone,2,2-di...

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

~%

(1-cyclopropylidene-2,2-dimethoxyethyl)benzene Structure

(1-cyclopropyli...

Ethanone,2,2-dimethoxy-1-phenyl- Structure

Ethanone,2,2-di...

(3-Bromopropyl)(triphenyl)phosphonium bromide Structure

(3-Bromopropyl)...

~%

N/A Structure

(1-cyclopropylidene-2,2-dimethoxyethyl)benzene Structure

(1-cyclopropyli...

2-cyclopropylidene-1,1-dimethoxycyclohexane Structure

2-cyclopropylid...

~60%

2-cyclopropylidenecyclohexan-1-one Structure

2-cyclopropylid...

2,2-dimethoxycyclohexan-1-one Structure

2,2-dimethoxycy...

~%

2-cyclopropylidenecyclohexan-1-one Structure

2-cyclopropylid...