Processes for preparing functionalized alkyllithium compounds

A process for the preparation of functionalized alkyllithium compounds, comprising reacting in an inert solvent a protected functionalized alkyl halide of the formula

• X--Z--T--[A(R.sup.1 R.sup.2 R.sup.3)].sub.m
• wherein X is halide;
• Z is a branched or straight chain hydrocarbon group containing 3-25 carbon atoms, optionally containing aryl or substituted aryl groups;
• T is oxygen, sulfur, or nitrogen;
• A is an element selected from Group IVa of the Periodic Table of Elements;
• R.sup.1, R.sup.2, and R.sup.3 are each independently selected from hydrogen, alkyl, substituted alkyl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, aryl or substituted aryl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, and cycloalkyl and substituted cycloalkyl containing 5 to 12 carbon atoms;
• and m is dependent on the valence of T and varies from one when T is oxygen or sulfur to two when T is nitrogen, with lithium in the presence of a catalytic compound selected from the group consisting of tetrahydrofuran, tert-butyl methyl ether, ethylene glycol diethyl ether, triethylamine, and hexamethyldisiloxane to produce a functionalized alkyllithium compound.

A composition comprising:

• a functionalized alkylalkali metal compound of the formula
• M--Q.sub.n --Z--T--[A(R.sup.1 R.sup.2 R.sup.3)].sub.m
• wherein M is an alkali metal;
• Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic hydrocarbons, and mixtures thereof;
• n is an integer from 0 to 5;
• Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups;
• T is oxygen, sulfur, or nitrogen;
• A is an element selected from Group IVa of the Periodic Table of Elements;
• R.sup.1, R.sup.2, and R.sup.3 are each independently selected from hydrogen, alkyl, substituted alkyl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, aryl or substituted aryl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, and cycloalkyl and substituted cycloalkyl containing 5 to 12 carbon atoms;
• and m is dependent on the valence of T and varies from one when T is oxygen or sulfur to two when T is nitrogen;
• and
• a compound of the formula
• (RR.sup.1 R.sup.2 M.sup.a).sub.y A(R.sup.3).sub.x
• wherein R, R.sup.1 and R.sup.2 are each independently selected from the group consisting of hydrogen, halogen, alkyl or alkenyl groups containing one to thirteen carbon atoms;
• R.sup.3 is independently selected from aryl groups containing 6 to 18 carbon atoms, four to six-membered heterocyclic carbon containing groups containing one to two heteroatoms selected from oxygen, nitrogen and sulfur;
• hydroxyalkyl, alkoxyalkyl, monoalkylaminoalkyl, dialkylaminoalkyl, and dialkylphosphinoalkyl groups containing two to thirteen carbon atoms;
• M.sup.a is an element selected from Group IVA of the Periodic Table of Elements;
• A is selected from oxygen, sulfur, nitrogen, and phosphorus;
• x+y equal the valence of A;
• and x and y may independently have a value from zero to three, in an inert solvent.

A composition comprising a functionalized alkylalkali metal compound of the formula

• M--Q.sub.n --Z--T--[A(R.sup.1 R.sup.2 R.sup.3)].sub.m
• wherein M is an alkali metal;
• Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic hydrocarbons, and mixtures thereof;
• n is an integer from 0 to 5;
• Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups;
• T is oxygen, sulfur, or nitrogen;
• A is an element selected from Group IVa of the Periodic Table of Elements;
• R.sup.1, R.sup.2, and R.sup.3 are each independently selected from hydrogen, alkyl, substituted alkyl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, aryl or substituted aryl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, and cycloalkyl and substituted cycloalkyl containing 5 to 12 carbon atoms;
• and m is dependent on the valence of T and varies from one when T is oxygen or sulfur to two when T is nitrogen, prepared by reacting in an inert solvent a protected functionalized alkyl halide with an alkali metal in the presence of a catalytic compound of the formula
• (RR.sup.1 R.sup.2 M.sup.a).sub.y A(R.sup.3).sub.x
• wherein R, R.sup.1 and R.sup.2 are each independently selected from the group consisting of hydrogen, halogen, alkyl or alkenyl groups containing one to thirteen carbon atoms;
• R.sup.3 is independently selected from aryl groups containing 6 to 18 carbon atoms, four to six-membered heterocyclic carbon containing groups containing one to two heteroatoms selected from oxygen, nitrogen and sulfur;
• hydroxyalkyl, alkoxyalkyl, monoalkylaminoalkyl, dialkylaminoalkyl and dialkylphosphinoalkyl groups containing two to thirteen carbon atoms;
• M.sup.a is an element selected from Group IVA of the Periodic Table of Elements;
• A is selected from oxygen, sulfur, nitrogen, and phosphorus;
• x+y equal the valence of A;
• and x and y may independently have a value from zero to three.