Provided is a method that allows for a safer production of a naphthylsilole for use as a starting material for GNR, which involves reacting a compound of formula (1):

##STR00001##

(wherein R.sup.1a and R.sup.1b are the same or different and represent a hydrogen atom, an alkyl group, a cycloalkyl group, a (poly)ether group, an ester group, a halogen atom, an aromatic hydrocarbon group, or a heterocyclic group; R.sup.1a and R.sup.1b are optionally bound to each other to form a ring; R.sup.2 represents an aromatic hydrocarbon ring or a heterocyclic ring; and X represents a bromine or iodine atom) with a lanthanide- and lithium-containing ate complex to produce a lanthanide complex of the compound of formula (1); and then reacting it with a silyl compound of formula (2):

R.sup.3aR.sup.3bSiCl.sub.2  (2)

(wherein R.sup.3a and R.sup.3b are the same or different and represent an optionally branched C.sub.1-C.sub.4 alkyl group or a phenyl group).

Provided is a method that allows for a safer production of a naphthylsilole for use as a starting material for GNR, which involves reacting a compound of formula (1):

##STR00001##

(wherein R.sup.1a and R.sup.1b are the same or different and represent a hydrogen atom, an alkyl group, a cycloalkyl group, a (poly)ether group, an ester group, a halogen atom, an aromatic hydrocarbon group, or a heterocyclic group; R.sup.1a and R.sup.1b are optionally bound to each other to form a ring; R.sup.2 represents an aromatic hydrocarbon ring or a heterocyclic ring; and X represents a bromine or iodine atom) with a lanthanide- and lithium-containing ate complex to produce a lanthanide complex of the compound of formula (1); and then reacting it with a silyl compound of formula (2):

R.sup.3aR.sup.3bSiCl.sub.2  (2)

(wherein R.sup.3a and R.sup.3b are the same or different and represent an optionally branched C.sub.1-C.sub.4 alkyl group or a phenyl group).

According to the present invention, a fluorine-containing (cyclo)alkenyl zinc halide compound can be obtained in a high yield by reacting a halogenated olefin compound represented by formula (2):

##STR00001##

wherein R.sup.1, R.sup.2, and R.sup.3 are as defined above, X.sup.2 represents a halogen atom, and a single bond expressed with a wavy line indicates that the steric configuration with respect to a double bond to which the single bond is connected is E configuration, Z configuration, or a mixture of E configuration and Z configuration in any ratio, with a zinc halide compound represented by formula (3): ZnX.sup.1 (3), wherein X.sup.1 is as defined above, in the presence of a zerovalent alkali metal.

A method for producing at least one compound of a fluorine-containing olefin compound (51) or a fluorine-containing olefin compound (52) includes performing a reaction of a fluorine-containing olefin compound (21) with an olefin compound (31) in the presence of a metal-carbene complex compound having an olefin metathesis reaction activity and an olefin compound (41) or (42).

##STR00001##

A method for producing at least one compound of a fluorine-containing olefin compound (51) or a fluorine-containing olefin compound (52) includes performing a reaction of a fluorine-containing olefin compound (21) with an olefin compound (31) in the presence of a metal-carbene complex compound having an olefin metathesis reaction activity and an olefin compound (41) or (42).

##STR00001##

The invention relates to bimesogenic compounds of formula I

##STR00001##

wherein R.sup.11, R.sup.12, MG.sup.11, MG.sup.12 and CG.sup.1 have the meaning given in claim 1, to the use of bimesogenic compounds of formula I in liquid crystal media and particular to flexoelectric liquid crystal devices comprising a liquid crystal medium according to the present invention.

The invention relates to bimesogenic compounds of formula I

##STR00001##

wherein R.sup.11, R.sup.12, MG.sup.11, MG.sup.12 and CG.sup.1 have the meaning given in claim 1, to the use of bimesogenic compounds of formula I in liquid crystal media and particular to flexoelectric liquid crystal devices comprising a liquid crystal medium according to the present invention.

The present invention relates to a novel process for the preparation of 9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-ylamine which process comprises a) reacting cyclopentadiene in the presence of a radical initiator and CXCl.sub.3, wherein X is chloro or bromo, to a compound of formula II ##STR00001## aa) reacting cyclopentadiene with CXCl.sub.3, wherein X is chloro, in the presence of a metal catalyst to a compound of formula II ##STR00002## wherein X is chloro, b) reacting the compound of formula II with a base in the presence of an appropriate solvent to the compound of formula III ##STR00003## c) and converting the compound of formula III in the presence of 1,2-dehydro-6-nitrobenzene to the compound of formula IV ##STR00004## and d) hydrogenating the compound of formula IV in the presence of a metal catalyst.

The present invention relates to a novel process for the preparation of 9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-ylamine which process comprises a) reacting cyclopentadiene in the presence of a radical initiator and CXCl.sub.3, wherein X is chloro or bromo, to a compound of formula II ##STR00001## aa) reacting cyclopentadiene with CXCl.sub.3, wherein X is chloro, in the presence of a metal catalyst to a compound of formula II ##STR00002## wherein X is chloro, b) reacting the compound of formula II with a base in the presence of an appropriate solvent to the compound of formula III ##STR00003## c) and converting the compound of formula III in the presence of 1,2-dehydro-6-nitrobenzene to the compound of formula IV ##STR00004## and d) hydrogenating the compound of formula IV in the presence of a metal catalyst.

The present invention relates to a novel process for the preparation of 9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-ylamine which process comprises a) reacting cyclopentadiene in the presence of a radical initiator and CXCl.sub.3, wherein X is chloro or bromo, to a compound of formula II ##STR00001## aa) reacting cyclopentadiene with CXCl.sub.3, wherein X is chloro, in the presence of a metal catalyst to a compound of formula II ##STR00002## wherein X is chloro, b) reacting the compound of formula II with a base in the presence of an appropriate solvent to the compound of formula III ##STR00003## c) and converting the compound of formula III in the presence of 1,2-dehydro-6-nitrobenzene to the compound of formula IV ##STR00004## and d) hydrogenating the compound of formula IV in the presence of a metal catalyst.