The present teachings are directed at 1,1-disubstituted alkene monomers (e.g., methylene beta-diketone monomers), methods for producing the same, and compositions and products formed therefrom. In the method for producing the monomer, a beta-diketone is preferably reacted with a source of formaldehyde in a modified Knoevenagel reaction optionally in the presence of an acidic or basic catalyst, and optionally in the presence of an acidic or non-acidic solvent, to form reaction complex. The reaction complex may be an oligomeric complex. The reaction complex is subjected to vaporization in order to isolate the monomer. The monomer(s) may be employed in compositions and products, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g., fibers, films, sheets, medical polymers, composite polymers and surfactants).

The present teachings are directed at 1,1-disubstituted alkene monomers (e.g., methylene beta-diketone monomers), methods for producing the same, and compositions and products formed therefrom. In the method for producing the monomer, a beta-diketone is preferably reacted with a source of formaldehyde in a modified Knoevenagel reaction optionally in the presence of an acidic or basic catalyst, and optionally in the presence of an acidic or non-acidic solvent, to form reaction complex. The reaction complex may be an oligomeric complex. The reaction complex is subjected to vaporization in order to isolate the monomer. The monomer(s) may be employed in compositions and products, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g., fibers, films, sheets, medical polymers, composite polymers and surfactants).

A process for preparation of 3-Trifluoromethyl acetophenone oxime of formula I includes reacting an isomeric mixture of halo benzotrifluoride with Mg metal in an organic solvent in presence of a catalyst to obtain a Grignard complex. The Grignard complex is reacted with a ketene in hydrocarbon solvent in presence of transition metal ligand-acid complex to obtain an isomeric mixture of trifluoromethyl acetophenone. Finally, the isomeric mixture of trifluoromethyl acetophenone is reacted with hydroxylamine salt to obtain compound of formula I.

A process for preparation of 3-Trifluoromethyl acetophenone oxime of formula I includes reacting an isomeric mixture of halo benzotrifluoride with Mg metal in an organic solvent in presence of a catalyst to obtain a Grignard complex. The Grignard complex is reacted with a ketene in hydrocarbon solvent in presence of transition metal ligand-acid complex to obtain an isomeric mixture of trifluoromethyl acetophenone. Finally, the isomeric mixture of trifluoromethyl acetophenone is reacted with hydroxylamine salt to obtain compound of formula I.

The invention discloses a method for preparations of fluoro, chloro and fluorochloro alkylated compounds by homogeneous Pd catalyzed fluoro, chloro and fluorochloro alkylation with fluoro, chloro and fluorochloroalkyl halides in the presence of di(1-adamantyl)-adamantyl-n-butylphosphine and in the presence of 2,2,6,6-tetramethylpiperdine 1-oxyl.

The invention relates to a process for the preparation of a compound of formula I comprising a) reacting a compound of formula II in the presence of magnesium or an organometallic reagent of formula III R.sub.1M.sup.2X (III), wherein R.sub.1 is C.sub.I-C.sub.4alkyl; M.sup.2 is Li or Mg and X is halogen or absent; with a compound of formula IV CF.sub.3-C(O)-R.sub.2 (IV), wherein R.sub.2 is halogen, hydroxyl, C.sub.I-C.sub.4alkoxy, (di-C.sub.I-C.sub.4alkyl)amino, OC(O)CF.sub.3, phenoxy or OM.sup.1; wherein M.sup.1 is Lithium, Magnesium, Sodium or Potassium; to a compound of formula V, and b) reacting the compound of formula V with alkali metal fluoride in the presence of catalytic amounts of a phase transfer catalyst in the presence of a polar solvent to the compound of formula I.

##STR00001##

The invention relates to a process for the preparation of a compound of formula I comprising a) reacting a compound of formula II in the presence of magnesium or an organometallic reagent of formula III R.sub.1M.sup.2X (III), wherein R.sub.1 is C.sub.I-C.sub.4alkyl; M.sup.2 is Li or Mg and X is halogen or absent; with a compound of formula IV CF.sub.3-C(O)-R.sub.2 (IV), wherein R.sub.2 is halogen, hydroxyl, C.sub.I-C.sub.4alkoxy, (di-C.sub.I-C.sub.4alkyl)amino, OC(O)CF.sub.3, phenoxy or OM.sup.1; wherein M.sup.1 is Lithium, Magnesium, Sodium or Potassium; to a compound of formula V, and b) reacting the compound of formula V with alkali metal fluoride in the presence of catalytic amounts of a phase transfer catalyst in the presence of a polar solvent to the compound of formula I.

##STR00001##

The invention relates to a process for the preparation of a compound of formula I comprising a) reacting a compound of formula II in the presence of magnesium or an organometallic reagent of formula III R.sub.1M.sup.2X (III), wherein R.sub.1 is C.sub.I-C.sub.4alkyl; M.sup.2 is Li or Mg and X is halogen or absent; with a compound of formula IV CF.sub.3-C(O)-R.sub.2 (IV), wherein R.sub.2 is halogen, hydroxyl, C.sub.I-C.sub.4alkoxy, (di-C.sub.I-C.sub.4alkyl)amino, OC(O)CF.sub.3, phenoxy or OM.sup.1; wherein M.sup.1 is Lithium, Magnesium, Sodium or Potassium; to a compound of formula V, and b) reacting the compound of formula V with alkali metal fluoride in the presence of catalytic amounts of a phase transfer catalyst in the presence of a polar solvent to the compound of formula I.

##STR00001##

To provide a liquid crystal compound satisfying at least one of physical properties such as a high stability to heat, light and so forth, a high clearing point, a low minimum temperature of a liquid crystal phase, a small viscosity, a suitable optical anisotropy, a large dielectric anisotropy, a suitable elastic constant and an excellent compatibility with other liquid crystal compounds; a liquid crystal composition containing the compound; and a liquid crystal display device including the composition. The compound is represented by formula (1): ##STR00001##
wherein, for example, Ra and Rb are alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons; A.sup.1, A.sup.2 and A.sup.3 are 1,4-cyclohexylene or 1,4-phenylene; Z.sup.1 and Z.sup.2 are single bonds, —(CH.sub.2).sub.2—, —CH═CH—, —COO—, —OCO—, —CF.sub.2O—, —OCF.sub.2—, —CH.sub.2O— or —OCH.sub.2—; Y.sup.1 is —CF.sub.2H or —CF.sub.3; Y.sup.2 is fluorine; and a, b and d are 0, 1, 2 or 3, and c is 1 or 3.

To provide a liquid crystal compound satisfying at least one of physical properties such as a high stability to heat, light and so forth, a high clearing point, a low minimum temperature of a liquid crystal phase, a small viscosity, a suitable optical anisotropy, a large dielectric anisotropy, a suitable elastic constant and an excellent compatibility with other liquid crystal compounds; a liquid crystal composition containing the compound; and a liquid crystal display device including the composition. The compound is represented by formula (1): ##STR00001##
wherein, for example, Ra and Rb are alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons or alkoxy having 1 to 9 carbons; A.sup.1, A.sup.2 and A.sup.3 are 1,4-cyclohexylene or 1,4-phenylene; Z.sup.1 and Z.sup.2 are single bonds, —(CH.sub.2).sub.2—, —CH═CH—, —COO—, —OCO—, —CF.sub.2O—, —OCF.sub.2—, —CH.sub.2O— or —OCH.sub.2—; Y.sup.1 is —CF.sub.2H or —CF.sub.3; Y.sup.2 is fluorine; and a, b and d are 0, 1, 2 or 3, and c is 1 or 3.