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

Synthesis

A convenient general access to methyl 2-chloro-2-cyclopropylidenacetates, reactive Michael acceptors and cycloaddends

T Liese, S Teichmann, A de Meijere

Index: Liese, Thomas; Teichmann, Stephan; Meijere, Armin de Synthesis, 1988 , # 1 p. 25 - 32

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Citation Number: 1

Abstract

The reaction of 1-chloro-1-(trich10rovinyl) eyclopropanes l with potassium hydroxidc/methanol or sodium rnethoxide/methanol yields trimethyl 2-chloro-2- eyclopropylidenorthoacetates 7. which can be quan-titatively converted to the corresponding esters 8 by acid treatment. The methyl 2-chloro-2-cyclopropylidenacetates 8 are highly reactive Mi-chael acceptors, which readily undergo 1.4-addition with soft nucleophilcs ...

1-(1-chloro-2,2,2-trimethoxyethylidene)-2-ethylcyclopropane Structure

1-(1-chloro-2,2...

~96%

methyl 2-chloro-2-(2-ethylcyclopropylidene)acetate Structure

methyl 2-chloro...

1-chloro-2-ethyl-1-(1,2,2-trichloroethenyl)cyclopropane Structure

1-chloro-2-ethy...

~%

methyl 2-chloro-2-(2-ethylcyclopropylidene)acetate Structure

methyl 2-chloro...

1-(1-chloro-2,2,2-trimethoxyethylidene)-2-methylcyclopropane Structure

1-(1-chloro-2,2...

~78%

methyl 2-chloro-2-(2-methylcyclopropylidene)acetate Structure

methyl 2-chloro...

1-chloro-2-methyl-1-(1,2,2-trichloroethenyl)cyclopropane Structure

1-chloro-2-meth...

~%

methyl 2-chloro-2-(2-methylcyclopropylidene)acetate Structure

methyl 2-chloro...

Methanol Structure

1-chloro-2-ethyl-1-(1,2,2-trichloroethenyl)cyclopropane Structure

1-chloro-2-ethy...

~53%

1-(1-chloro-2,2,2-trimethoxyethylidene)-2-ethylcyclopropane Structure

1-(1-chloro-2,2...

Methanol Structure

1-chloro-2-methyl-1-(1,2,2-trichloroethenyl)cyclopropane Structure

1-chloro-2-meth...

~60%

1-(1-chloro-2,2,2-trimethoxyethylidene)-2-methylcyclopropane Structure

1-(1-chloro-2,2...

Methanol Structure

7-chloro-7-(1,2,2-trichloroethenyl)bicyclo[4.1.0]heptane Structure

7-chloro-7-(1,2...

~23%

7-(1-chloro-2,2,2-trimethoxyethylidene)bicyclo[4.1.0]heptane Structure

7-(1-chloro-2,2...

Methanol Structure

1-CHLORO-1-(TRICHLOROVINYL) CYCLOPROPANE Structure

1-CHLORO-1-(TRI...

~60%

(1-chloro-2,2,2-trimethoxyethylidene)cyclopropane Structure

(1-chloro-2,2,2...

3-(1-chloro-2,2,2-trimethoxyethylidene)-1,1,2,2-tetramethylcyclopropane Structure

3-(1-chloro-2,2...

~%

2-chloro-2-(2,2,3,3-tetramethylcyclopropylidene)acetic acid Structure

2-chloro-2-(2,2...

(1-chloro-2,2,2-trimethoxyethylidene)cyclopropane Structure

(1-chloro-2,2,2...

~96%

Methyl 2-chloro-2-cyclopropylideneacetate Structure

Methyl 2-chloro...

1-CHLORO-1-(TRICHLOROVINYL) CYCLOPROPANE Structure

1-CHLORO-1-(TRI...

~%

Methyl 2-chloro-2-cyclopropylideneacetate Structure

Methyl 2-chloro...

7-(1-chloro-2,2,2-trimethoxyethylidene)bicyclo[4.1.0]heptane Structure

7-(1-chloro-2,2...

~93%

methyl 2-(7-bicyclo[4.1.0]heptanylidene)-2-chloroacetate Structure

methyl 2-(7-bic...

7-chloro-7-(1,2,2-trichloroethenyl)bicyclo[4.1.0]heptane Structure

7-chloro-7-(1,2...

~%

methyl 2-(7-bicyclo[4.1.0]heptanylidene)-2-chloroacetate Structure

methyl 2-(7-bic...

Methanol Structure

1-chloro-2,2,3-trimethyl-1-(1,2,2-trichloroethenyl)cyclopropane Structure

1-chloro-2,2,3-...

~40%

2-(1-chloro-2,2,2-trimethoxyethylidene)-1,1,3-trimethylcyclopropane Structure

2-(1-chloro-2,2...

2-(1-chloro-2,2,2-trimethoxyethylidene)-1,1,3-trimethylcyclopropane Structure

2-(1-chloro-2,2...

~75%

methyl 2-chloro-2-(2,2,3-trimethylcyclopropylidene)acetate Structure

methyl 2-chloro...

1-chloro-2,2,3-trimethyl-1-(1,2,2-trichloroethenyl)cyclopropane Structure

1-chloro-2,2,3-...

~%

methyl 2-chloro-2-(2,2,3-trimethylcyclopropylidene)acetate Structure

methyl 2-chloro...