Preparation of cyclopropane-carboxylic acid derivatives and intermediates therefor
AssigneeBayer Aktiengesellschaft
InventorsMichael Hanack, Theodor Stoll
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Abstract
A perfluoroalkane-sulphinic acid of the formula R.sub.F --SO.sub.2 H is reacted with a diene at -20.degree. to +20.degree. C. to form the new intermediate ##STR1## in which R.sup.3 -R.sup.8 are hydrogen or various organic radicals or double bonds, and that is reacted with a .beta.,.beta.-dimethyl-acrylic acid derivative of the formula ##STR2## in the presence of a base at a temperature between about -20.degree. and +30.degree. C. to produce a cyclopropane carboxylic acid derivative of the formula ##STR3## in which Z is alkoxycarbonyl or cyano and R.sup.1 and R.sup.2 are hydrogen or various organic radicals. The products are known intermediates for insecticides.
Claims11
A process for the preparation of a cyclopropane-1-carboxylic acid derivative of the formula ##STR13## in which Z represents alkoxycarbonyl or cyano,
- R.sup.1 represents hydrogen or alkenyl and
- R.sup.2 represents hydrogen, or
- R.sup.1 and R.sup.2 together represent cycloalkyl or cycloalkenyl, onto which a benzene ring can optionally be fused,
- comprising reacting a perfluoroalkyl sulphone of the formula ##STR14## in which R represents the radical --SO.sub.2 --R.sub.F,
- R.sup.3 represents hydrogen or alkyl,
- R.sup.4 represents alkyl or, together with R.sup.8, forms and alkenediyl bridge, the double bond of which is optionally fused onto a benzene ring,
- R.sup.5 and R.sup.6 either represent hydrogen or together form a double bond,
- R.sup.7 represents hydrogen or alkyl,
- R.sup.8 represents hydrogen or alkyl and
- R.sub.F represents perfluoroalkyl, with the proviso that either R.sup.5 and R.sup.6 form a double bond or R.sup.8 and R.sup.4 form an alkenediyl bridge, the double bond of which is optionally fused onto a benzene ring, with a .beta.,.beta.-dimethyl-acrylic acid derivative of the formula ##STR15## in the presence of a base at a temperature between about -20.degree. C. and +30.degree. C.
A process for the preparation of a perfluoroalkyl sulphone of the formula ##STR19## in which R represents the radical --SO.sub.2 --R.sub.F,
- R.sup.3 represents hydrogen or alkyl,
- R.sup.4 represents alkyl or, together with R.sup.8, forms an alkenediyl bridge, the double bond of which is optionally fused onto a benzene ring,
- R.sup.5 and R.sup.6 either represent hydrogen or together form a double bond,
- R.sup.7 represents hydrogen or alkyl,
- R.sup.8 represents hydrogen or alkyl and
- R.sub.F represents perfluoroalkyl,
- comprising reacting a perfluoroalkane-sulphinic acid of the formula R.sub.F --SO.sub.2 H
- in which R.sub.F is perfluoroalkyl,
- with a diene of the formula ##STR20## in which R.sup.9 --R.sup.13 each independently is hydrogen or alkyl, it being possible for R.sup.9, together with R.sup.13, to represent an alkylene bridge, onto which a cycloalkene ring is optionally fused,
- at a temperature between about -20.degree. and +20.degree. C.
Dependencies are inferred from the claim text.