Provided is a process for the mono-alkylation of cyclopentadiene, utilizing a cyclopentadiene magnesium halide and a metal salt of an alkyl or aryl sulfonate as co-reactant with an alkyl halide alkylating reactant. The process provides facile methodology for the mono-alkylation of cyclopentadiene, with conversions as high as about 96 percent and selectivity for mono-alkylation (over higher level alkylation, such as di- or tri-) as high as about 99%.

The present invention relates to a process for preparing a 3,7-dimethylalkane compound (3): wherein n is 5 or 6, the process comprising: subjecting a nucleophilic reagent, 2,6-dimethyloctyl compound (1): wherein M.sup.1 represents Li, Mg Z.sup.1, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 2,6-dimethyloctyl group, to a coupling reaction with an electrophilic alkyl reagent (2): wherein X.sup.1 represents a halogen atom or a p-toluenesulfonate group, and “n” is as defined above, to form the 3,7-dimethylalkane compound (3).

##STR00001##

The present invention relates to a process for preparing a 3,7-dimethylalkane compound (3): wherein n is 5 or 6, the process comprising: subjecting a nucleophilic reagent, 2,6-dimethyloctyl compound (1): wherein M.sup.1 represents Li, Mg Z.sup.1, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 2,6-dimethyloctyl group, to a coupling reaction with an electrophilic alkyl reagent (2): wherein X.sup.1 represents a halogen atom or a p-toluenesulfonate group, and “n” is as defined above, to form the 3,7-dimethylalkane compound (3).

##STR00001##

The present invention relates to a process for preparing a 3,7-dimethylalkane compound (3): wherein n is 5 or 6, the process comprising: subjecting a nucleophilic reagent, 2,6-dimethyloctyl compound (1): wherein M.sup.1 represents Li, Mg Z.sup.1, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 2,6-dimethyloctyl group, to a coupling reaction with an electrophilic alkyl reagent (2): wherein X.sup.1 represents a halogen atom or a p-toluenesulfonate group, and “n” is as defined above, to form the 3,7-dimethylalkane compound (3). ##STR00001##

The present invention relates to a process for preparing a 3,7-dimethylalkane compound (3): wherein n is 5 or 6, the process comprising: subjecting a nucleophilic reagent, 2,6-dimethyloctyl compound (1): wherein M.sup.1 represents Li, Mg Z.sup.1, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 2,6-dimethyloctyl group, to a coupling reaction with an electrophilic alkyl reagent (2): wherein X.sup.1 represents a halogen atom or a p-toluenesulfonate group, and “n” is as defined above, to form the 3,7-dimethylalkane compound (3). ##STR00001##

The disclosure provides methodology for the synthesis of mono-alkylated cyclopentadiene structures, which can be obtained via fulvene intermediates. In one embodiment, the cyclopentadiene ring is substituted with a trialkylsilyl moiety, which enables the further reaction with certain metal halides to form metal adducts. For example, the monoalkyl cyclopentadienes substituted with a trimethylsilyl group can be reacted with TiCl.sub.4 to provide R*CpTiCl.sub.3 complexes, wherein R* is a group of the formula

##STR00001##

wherein R.sup.1 and R.sup.2 are as defined herein.

The disclosure provides methodology for the synthesis of mono-alkylated cyclopentadiene structures, which can be obtained via fulvene intermediates. In one embodiment, the cyclopentadiene ring is substituted with a trialkylsilyl moiety, which enables the further reaction with certain metal halides to form metal adducts. For example, the monoalkyl cyclopentadienes substituted with a trimethylsilyl group can be reacted with TiCl.sub.4 to provide R*CpTiCl.sub.3 complexes, wherein R* is a group of the formula

##STR00001##

wherein R.sup.1 and R.sup.2 are as defined herein.

A method for producing an organometallic nucleophile includes reacting an organohalide and a metal or metal compound with each other by a mechanochemical process in the presence of an ether compound in an amount of 0.5 to 10.0 equivalents relative to 1 equivalent of the organohalide. By utilizing the method, a method for producing an organometallic nucleophile can be performed without using a large-scale apparatus, a reaction method for reactions between an organometallic nucleophile and various organic electrophiles can be performed by an efficient and simplified means, and a simplified method for producing an organometallic nucleophile can be performed with high reactivity.

A method for producing an organometallic nucleophile includes reacting an organohalide and a metal or metal compound with each other by a mechanochemical process in the presence of an ether compound in an amount of 0.5 to 10.0 equivalents relative to 1 equivalent of the organohalide. By utilizing the method, a method for producing an organometallic nucleophile can be performed without using a large-scale apparatus, a reaction method for reactions between an organometallic nucleophile and various organic electrophiles can be performed by an efficient and simplified means, and a simplified method for producing an organometallic nucleophile can be performed with high reactivity.

Provided is a process for the mono-alkylation of cyclopentadiene, utilizing a cyclopentadiene magnesium halide and a metal salt of an alkyl or aryl sulfonate as co-reactant with an alkyl halide alkylating reactant. The process provides facile methodology for the mono-alkylation of cyclopentadiene, with conversions as high as about 96 percent and selectivity for mono-alkylation (over higher level alkylation, such as di- or tri-) as high as about 99%.