An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound.

The above object can be achieved by a method for producing a compound represented by formula (1):

##STR00001## wherein R.sup.1 represents an organic group, R.sup.A represents hydrogen or fluorine, R.sup.4a represents hydrogen or an organic group, R.sup.4b represents hydrogen or an organic group, R.sup.5a represents hydrogen or an organic group, R.sup.5b represents hydrogen or an organic group, and R.sup.2 represents hydrogen or an organic group; R.sup.2 is optionally connected to R.sup.4a to form a ring; the method comprising step A of reacting a compound represented by formula (2):

##STR00002## wherein X.sup.1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3):

##STR00003## wherein X.sup.2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.

A method for preparing isotopologues and/or stereoisotopomers of cyclic and heterocyclic alkenes and dienes is described. The method provides regio- and/or stereospecific addition of hydrogen, deuterium, tritium and a variety of other substituents to arenes, heteroarenes, and alicyclic compounds that have multiple carbon-carbon double bonds, thereby providing discrete isotopologues and stereoisotopomers of cyclic and heterocyclic alkenes and dienes with high isotopic purity and in high enantiomeric excess. Also described are isotopologues and stereoisotopomers of cyclic and heterocyclic alkenes and dienes, such as isotopologues and stereoisotopomers of cyclohexene and tetrahydropyridine, as well as products thereof, such as isotopologues and stereoisotopomers of piperidines and piperidine-containing compounds, such as methylphenidate. In addition, a method of determining the absolute configuration of stereoisotopomers of cyclohexenes is described.

A method for preparing isotopologues and/or stereoisotopomers of cyclic and heterocyclic alkenes and dienes is described. The method provides regio- and/or stereospecific addition of hydrogen, deuterium, tritium and a variety of other substituents to arenes, heteroarenes, and alicyclic compounds that have multiple carbon-carbon double bonds, thereby providing discrete isotopologues and stereoisotopomers of cyclic and heterocyclic alkenes and dienes with high isotopic purity and in high enantiomeric excess. Also described are isotopologues and stereoisotopomers of cyclic and heterocyclic alkenes and dienes, such as isotopologues and stereoisotopomers of cyclohexene and tetrahydropyridine, as well as products thereof, such as isotopologues and stereoisotopomers of piperidines and piperidine-containing compounds, such as methylphenidate. In addition, a method of determining the absolute configuration of stereoisotopomers of cyclohexenes is described.

Methods of hydromethylation of alkenes and ketones, including methods that use Tebbe's reagent. The methods may include contacting Cp.sub.2Ti(μ-Cl)(μ-CH.sub.2)AlMe.sub.2 and an alkene or a ketone to produce an intermediate product that may include a titanacyclobutane. The intermediate product may be contacted with an acid to produce a methylated product.

Methods of hydromethylation of alkenes and ketones, including methods that use Tebbe's reagent. The methods may include contacting Cp.sub.2Ti(μ-Cl)(μ-CH.sub.2)AlMe.sub.2 and an alkene or a ketone to produce an intermediate product that may include a titanacyclobutane. The intermediate product may be contacted with an acid to produce a methylated product.

The invention relates to a new process for the manufacture of fluoroaryl compounds and derivatives thereof, in particular of fluorobenzenes and derivatives thereof, and especially wherein said manufacture relates to an environmentally friendly production of the said compounds. Thus, the present invention overcomes the disadvantages of the prior art processes, and in a surprisingly simple and beneficial manner, and as compared to the prior art processes, in particular, the invention provides a more efficient and energy saving processes, and also provides a more environmentally friendly process, for the manufacture of nuclear fluorinated aromatics, and preferably of nuclear fluorinated fluorobenzenes. Accordingly, in one aspect of the invention, an industrially beneficial process for preparing fluorobenzenes from halobenzene precursors using HF to form hydrogen halide is provided by the present invention. A beneficial and surprisingly simple use of chlorobenzene as an industrially interesting starting material in the manufacture of fluorobenzene is provided.

The present invention provides a palladium(II) complex of formula (1). ##STR00001## R.sub.12, m, and X are described in the specification. The invention also provides a process for the preparation of the complex, and its use in carbon-carbon and carbon-heteroatom coupling reactions.

The present invention provides a palladium(II) complex of formula (1). ##STR00001## R.sub.12, m, and X are described in the specification. The invention also provides a process for the preparation of the complex, and its use in carbon-carbon and carbon-heteroatom coupling reactions.

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##