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

Liebigs Annalen der Chemie

Fragmentierung cyclischer Carboxonium??Ionen, IV Synthese von β??Oxa?螃?, δ??enonen

J Mattay, W Thünker, HD Scharf

Index: Mattay, Jochen; Thuenker, Walter; Scharf, Hans-Dieter Liebigs Annalen der Chemie, 1981 , # 6 p. 1105 - 1117

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Citation Number: 3

Abstract

Abstract Die protonenkatalysierte Fragmentierung der 4-Methylen-1, 3-dioxolane 2 mit schwachen Säuren (pK> 4.3) oder mit schwach sauren Ionenaustauschern führt in guten Ausbeuten zu den β-Oxa-γ, δ-enonen 5, die damit erstmals einfach und allgemein zugänglich werden.

Heptanal Structure

Epichlorohydrin Structure

Epichlorohydrin

~63%

1,3-Dioxolane, 4-(chloromethyl)-2-hexyl- Structure

1,3-Dioxolane, ...

Decanal Structure

Epichlorohydrin Structure

Epichlorohydrin

~58%

1,3-Dioxolane,4-(chloromethyl)-2-nonyl- Structure

1,3-Dioxolane,4...

2-methyl-5-chloromethyl-1,3-dioxolane Structure

2-methyl-5-chlo...

~61%

2-methyl-4-methylidene-1,3-dioxolane Structure

2-methyl-4-meth...

3,4-dibromobutan-2-ol Structure

3,4-dibromobuta...

~84%

2-(bromomethyl)-3-methyloxirane Structure

2-(bromomethyl)...

3-(bromomethyl)-2,2-dimethyloxirane Structure

3-(bromomethyl)...

~%

2,2,4,4-tetramethyl-5-methylidene-1,3-dioxolane Structure

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

2-Butanol,3,4-dibromo-2-methyl- Structure

2-Butanol,3,4-d...

~%

2,2,4,4-tetramethyl-5-methylidene-1,3-dioxolane Structure

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

2-(bromomethyl)-3,3-dimethyl-1,4-dioxaspiro[4.4]nonane Structure

2-(bromomethyl)...

~82%

3,3-dimethyl-2-methylidene-1,4-dioxaspiro[4.4]nonane Structure

3,3-dimethyl-2-...

3-(bromomethyl)-2,2-dimethyloxirane Structure

3-(bromomethyl)...

~%

3,3-dimethyl-2-methylidene-1,4-dioxaspiro[4.4]nonane Structure

3,3-dimethyl-2-...

2-Butanol,3,4-dibromo-2-methyl- Structure

2-Butanol,3,4-d...

~%

3,3-dimethyl-2-methylidene-1,4-dioxaspiro[4.4]nonane Structure

3,3-dimethyl-2-...

Cyclopentanone Structure

~%

3,3-dimethyl-2-methylidene-1,4-dioxaspiro[4.4]nonane Structure

3,3-dimethyl-2-...

2-Butanol,3,4-dibromo-2-methyl- Structure

2-Butanol,3,4-d...

~%

5-(bromomethyl)-2,2,4,4-tetramethyl-1,3-dioxolane Structure

5-(bromomethyl)...

3-(bromomethyl)-2,2-dimethyloxirane Structure

3-(bromomethyl)...

Cyclopentanone Structure

~68%

2-(bromomethyl)-3,3-dimethyl-1,4-dioxaspiro[4.4]nonane Structure

2-(bromomethyl)...

2-Butanol,3,4-dibromo-2-methyl- Structure

2-Butanol,3,4-d...

~%

2-(bromomethyl)-3,3-dimethyl-1,4-dioxaspiro[4.4]nonane Structure

2-(bromomethyl)...