Alkene, alkyne or cycloalkylene derivatives

Claim 2

A process for the manufacture of a compound of the formula wherein X has the formula or wherein ring A is phenyl, naphthyl or heterocyclic; wherein R l is hydrogen, alkyl or alkanoyl each of up to 6 carbon atoms or aroyl of up to 10 carbon atoms; wherein R 2 , R 3 and R 4 , which may be the same or different, each is an electron withdrawing substituent selected from halogeno, nitro, cyano and trifluoromethyl, and alkylthio, alkylsulphinyl and alkylsulphonyl each of up to 6 carbon atoms, or each is hydrogen or alkyl, alkoxy or dialkylamino each of up to 6 carbon atoms, provided that when ring A is phenyl or naphthyl at least one of R 2 , R 3 and R 4 is an electron-withdrawing substituent; wherein R 5 and R 6 , which may be the same or different, each is hydrogen, halogeno or alkyl of up to 6 carbon atoms, ; wherein R 7 is alkyl or halogenoalkyl each of up to 6 carbon atoms; and wherein R S has the formula wherein Y is straight- or branched-chain alkylene or alkenylene each of up to 6 carbon atoms; wherein Q is -O-, -S-, -SO- or -S0 2 -; and wherein R 9 is alkyl of up to 6 carbon atoms which contains one or more substituents selected from halogeno, cyano, hydroxy, amino, hydroxyimino, guanidino, ureido and carbamoyl; alkoxy, alkylamino, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbamoyl, alkoxyimino, alkanoyl, halogenoalkanoyl, alkanoylamino and alkylsulphonamido each of up to 6 carbon atoms; alkoxyalkoxy, dialkylamino and dialkylcarbamoyl each of up to 12 carbon atoms; aryl, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, aryloxyimino and aroyl each of up to 10 carbon atoms; heterocyclyl, heterocyclylthio, heterocyclylsulphinyl, heterocyclylsulphonyl, heterocyclyloxyimino and heterocyclylcarbonyl; and alkylenedioxy of to 2 to 4 carbon atoms wherein both oxygen atoms are attached to the same carbon atom of R 9 , charaterised by:- (a) for the manufacture of an alkene wherein R 1 is hydroxy and X is -CR 5 =C R 6- , the reaction of a compound of the formula: wherein A, R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings stated above with an organometallic compound of the formula R 8- M, wherein R 8 has the meaning stated above and M is a metallic group; or (b) for the manufacture of an alkene wherein R 1 is hydroxy, X is -CR 5 = CR 6 - and Y is -CH 2 -, the reaction of an epoxide of the formula: wherein A, R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings stated above, with a compound of the formula R 9- Q-H, wherein R 9 and Q have the meanings stated above or, when Q is -S-, with the corresponding isothiouronium salt of the formula ⊕ B⊖ wherein B⊖ is an anion; or (c) for the manufacture of a cycloalkylene derivative wherein X is , the reaction of a compound of the formula wherein A, R 2 , R 3 , R 4 , R 5 , R 6 and M have the meanings stated above, with a compound of the formula wherein R 7 and R 8 have the meanings stated above; or (d) for the manufacture of an alkyne of the invention wherein X is -C=C-, the reaction of a compound of the formula wherein A, R 1 , R 2 , R 3 and R 4 have the meanings stated above and wherein Z is a displaceable group, with a compound of the formula wherein R 1 , R 7 and R 8 have the meanings stated above; whereafter a compound wherein X is -C≡C- may be reduced to the corresponding compound wherein X is -CH=CH-; and whereafter:- (i) a compound wherein R 9 bears an amino substituent may be acylated to give the corresponding compound wherein R 9 bears an alkanoylamino, alkoxycarbonylamino or alkylsulphonamido substituent; (ii) a compound wherein R9 is alkyl substituted by alkanoyl may be reduced to the corresponding compound wherein R 9 is hydroxyalkyl; (iii) a compound wherein R 1 is alkyl may be prepared by the alkylation of the corresponding compound wherein R 1 is hydrogen. (iv) a compound wherein R 1 is alkanoyl or aroyl may be prepared by the acylation of the corresponding compound wherein R 1 is hydrogen; or (v) a compound wherein one or more of R 2 , R 3 , R 4 and a substituent in R9 is alkyl-sulphinyl or alkylsulphonyl, or a substituent in R 9 is arylsulphinyl, arylsulphonyl, heterocyclylsulphinyl or heterocyclylsulphonyl, or 0 is -SO- or -SO 2 -, may be prepared by the oxidation of the corresponding compound wherein one or more of R 2 , R 3 , R 4 and a substituent in R 9 is alkylthio, arylthio or heterocyclylthio, or Q is - S-, respectively.

Claim 3

A process as claimed in claim 1 wherein in the starting materials X is -CR 5 =CR 6- , in the trans- configuration, ring A is phenyl, one or two (the same or different) of R 2 , R 3 and R 4 are fluoro, chloro, cyano, trifluoromethyl or nitro, the others of R 2 , R 3 and R 4 being hydrogen, R 1 , R 5 and R 6 are all hydrogen, R 7 is trifluoromethyl, pentafluoroethyl, heptafluoropropyl, chloromethyl or dichloromethyl; Q is -S, -SO- or -S0 2 , Y is -CH 2 - and R 9 is straight-chain-alkyl of up to 4 carbon atoms which bears one or two substituents selected from chloro, cyano, hydroxy, amino, carbamoyl, methoxy, ethoxy, methylthio, methylsulphonyl, acetyl, acetamido, ureido, dimethylamino, dimethylcarbamoyl, phenyl, fluorophenyl, methylthiophenyl, methylsulphonylphenyl, naphthyl, methoxyphenoxy, phenylthio, methylthiophenylthio, methylsulphonylphenylthio, benzoyl, thenoyl, furyl, pyridyl, pyrazinyl, methylthiazolyl and 1,4- b enzodioxanyl; or which bears one such substituent and also three fluorine substituents on the terminal carbon atom; or which bears an ethylenedioxy or trimethylene-1,3-dioxy substituent; or which bears three fluorine substituents on the terminal carbon atom.

Claim 4

A process as claimed in claim 2 wherein in the starting materials ring A is 3,4-dichlorophenyl, 3-chloro-4-cyanophenyl, 4-cyano-3-trifluoromethylphenyl or 4-fluoro-3-trifluoromethylphenyl and R 7 is trifluoromethyl.