Disclosed herein is a novel method for preparing cyclophanes, comprising forming a disulfide cyclophane by contacting a linker moiety which includes two or more thiol groups, with a metal salt and an oxidant. The disulfide cyclophane is then desulfurized to form a thiacyclophane comprising thioether bridges. This thiacyclophane optionally may be further desulfurized to form an unsaturated hydrocarbon cyclophane, which can then be reduced to form a saturated hydrocarbon cyclophane. The various cyclophanes can be synthesized in a ring form, such as a dimer, trimer or tetramer etc., or they can be synthesized in a tetrahedral or larger structure. Also disclosed are novel cyclophanes formed by the disclosed method.

A phenol derivative of the present invention has a structure as represented by the formula (I):

##STR00001##

The functional groups are defined in the description. The phenol derivative can be used as the antioxidant in lubricating oil, lubricating grease, plastic, rubber, or can be used as the base oil of the lubricating oil and the lubricating grease and the antiwear additive of the lubricating oil and the lubricating grease.

A phenol derivative of the present invention has a structure as represented by the formula (I):

##STR00001##

The functional groups are defined in the description. The phenol derivative can be used as the antioxidant in lubricating oil, lubricating grease, plastic, rubber, or can be used as the base oil of the lubricating oil and the lubricating grease and the antiwear additive of the lubricating oil and the lubricating grease.

Provided herein is a compound of Formula (I-I), or a pharmaceutically acceptable salt thereof, wherein the variables are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I-I), and methods of using the compounds, e.g. in the treatment of CNS-related disorders. ##STR00001##

A phenol derivative of the present invention has a structure as represented by the formula (I): ##STR00001##
The functional groups are defined in the description. The phenol derivative can be used as the antioxidant in lubricating oil, lubricating grease, plastic, rubber, or can be used as the base oil of the lubricating oil and the lubricating grease and the antiwear additive of the lubricating oil and the lubricating grease.

A phenol derivative of the present invention has a structure as represented by the formula (I): ##STR00001##
The functional groups are defined in the description. The phenol derivative can be used as the antioxidant in lubricating oil, lubricating grease, plastic, rubber, or can be used as the base oil of the lubricating oil and the lubricating grease and the antiwear additive of the lubricating oil and the lubricating grease.

A compound represented by Formula (1) or (3).

##STR00001##

wherein R.sup.1 and R.sup.2 are each independently a hydrogen atom; a C1-6 alkyl group optionally having one or more substituents selected from the group consisting of a carboxy group and —OR.sup.5; a C2-6 alkyl group having one or more substituents selected from the group consisting of —NR.sup.6R.sup.7 and —N.sup.+R.sup.9R.sup.10R.sup.11; or —(CH.sub.2CH.sub.2O).sub.nR.sup.8;

##STR00002##

wherein R.sup.4 is a C1-6 alkyl group having one or more substituents selected from the group consisting of a carboxy group and —OR.sup.5; a C2-6 alkyl group having one or more substituents selected from the group consisting of —NR.sup.6R.sup.7 and —N.sup.+R.sup.9R.sup.10R.sup.11, or —(CH.sub.2CH.sub.2O).sub.nR.sup.8;
wherein R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are each independently a hydrogen atom or a C1-3 alkyl group; and n is an integer of 2 to 5.

A compound represented by Formula (1) or (3).

##STR00001##

wherein R.sup.1 and R.sup.2 are each independently a hydrogen atom; a C1-6 alkyl group optionally having one or more substituents selected from the group consisting of a carboxy group and —OR.sup.5; a C2-6 alkyl group having one or more substituents selected from the group consisting of —NR.sup.6R.sup.7 and —N.sup.+R.sup.9R.sup.10R.sup.11; or —(CH.sub.2CH.sub.2O).sub.nR.sup.8;

##STR00002##

wherein R.sup.4 is a C1-6 alkyl group having one or more substituents selected from the group consisting of a carboxy group and —OR.sup.5; a C2-6 alkyl group having one or more substituents selected from the group consisting of —NR.sup.6R.sup.7 and —N.sup.+R.sup.9R.sup.10R.sup.11, or —(CH.sub.2CH.sub.2O).sub.nR.sup.8;
wherein R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are each independently a hydrogen atom or a C1-3 alkyl group; and n is an integer of 2 to 5.

A process for preparation of thiocyclam base and salt. A method of manufacturing N,N-dimethyl-1,2,3-trithian-5-ylainine hydrochloride is described including the steps of: providing a mixture of thiosulfuric acid S, S′[2-(dimethylamino) trimethylene] ester monosodium salt and sodium hydroxide; adding an aqueous saline solution to the mixture of thiosulfuric acid S, S′-[2-(dimethylamino) trimethylene] ester monosodium salt and sodium hydroxide; separating the phases of the mixture; collecting the solids from the mixture using filtration; washing the solids with organic solvent; and drying the solids, where the dried solids are methyl-1,2,3-trithian-5-ylamine hydrochloride, and where the yield of the N,N-dimethyl-1,2,3-trithian-5-ylamine hydrochloride is increased by incorporation of a body charge of diatomaceous earth into the saline addition step, forming a mixture of the diatomaceous C earth with the composition of this step, and filtering the charged mixture through a diatomaceous earth media prior to the separation step.

A process for preparation of thiocyclam base and salt. A method of manufacturing N,N-dimethyl-1,2,3-trithian-5-ylainine hydrochloride is described including the steps of: providing a mixture of thiosulfuric acid S, S′[2-(dimethylamino) trimethylene] ester monosodium salt and sodium hydroxide; adding an aqueous saline solution to the mixture of thiosulfuric acid S, S′-[2-(dimethylamino) trimethylene] ester monosodium salt and sodium hydroxide; separating the phases of the mixture; collecting the solids from the mixture using filtration; washing the solids with organic solvent; and drying the solids, where the dried solids are methyl-1,2,3-trithian-5-ylamine hydrochloride, and where the yield of the N,N-dimethyl-1,2,3-trithian-5-ylamine hydrochloride is increased by incorporation of a body charge of diatomaceous earth into the saline addition step, forming a mixture of the diatomaceous C earth with the composition of this step, and filtering the charged mixture through a diatomaceous earth media prior to the separation step.