Preparation process of bis(1,2-diaryl-1,2-ethyolenedithiolato)ni

Details Preparation process of bis(1,2-diaryl-1,2-ethyolenedithiolato)ni Preparation process of bis(1,2-diaryl-1,2-ethyolenedithiolato)ni

1990-11-15

1993-01-26

Prescott, Arthur C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heavy metal containing

556138, C07F 1702

Patent

active

051824094

DESCRIPTION:

BRIEF SUMMARY
1. TECHNICAL FIELD

The present invention relates to a process for the preparation of bis(1,2-diaryl-1,2-ethylenedithiolato)nickel-based complex from benzil-based compounds or benzoin-based compounds.


2. BACKGROUND ART

Bis(1,2-diaryl-1,2-ethylenedithiolato)nickel-based complexes are compounds having characteristic absorption in the near-infrared region. These are a group of compounds used for light compensation filters for near-infrared radiation and optical recording discs. These complexes also have a property for deactivating a singlet oxygen and are employed for singlet oxygen quenchers such as light stabilizers or antioxidants of polyolefins and photodeterioration inhibitors of organic dyestuffs.
The common preparation process of these complexes is described, for example, in G. N. Schrauzer et al, J. Am. Chem. Soc., 87, 1483 (1965) and can be prepared by the following reaction process. ##STR1##
That is, a benzoin compound represented by the formula (III): ##STR2## wherein R is a hydrogen atom, methyl, methoxy or a chlorine atom, and is reacted with phosphorus pentasulfide by heating in dioxane. An intermediate phosphorus compound thus formed is cooled to the room temperature. After filtering off insoluble by-products, an aqueous solution of nickel chloride (II) is added and reacted by heating to obtain a nickel-based complex represented by the formula (IV): ##STR3## wherein R is the same as in the formula (III).
However, the process which uses dioxane as a solvent causes various side reactions and the desired product can be obtained in a low yield of about 35% at the most. Consequently, enhancement of the yield has been desired.


3. DISCLOSURE OF INVENTION

The object of the invention is to provide a preparation process for obtaining a bis(1,2-diaryl-1,2-ethylenedithiolato)nickel-based complex in a high yield by using a benzil-based compound or a benzoin-based compound as a raw material.
As a result of extensive investigation, it has been found that the object can be achieved by carrying out the reaction in a specific solvent. That is, the aspect of the invention is a process for the preparation of a bis(1,2-diaryl-1,2-ethylenedithiolato)nickel-based complex by reacting the above raw material with phosphorus pentasulfide in 1,3-dimethyl-2-imidazolidinone and successively reacting the resultant intermediate with nickel chloride.


4. BEST MODE FOR CARRYING OUT THE INVENTION

The bis(1,2-diaryl-1,2-ethylenedithiolato)nickel-based complex which is the object of the present invention is represented by the formula (I): ##STR4## where R.sup.1 and R.sup.2 are individually phenyl or naphthyl and may also have from one to three substituents individually selected from alkyl, cycloalkyl, aryl, alkoxy, phenoxy, hydroxy, alkylamino, arylamino, trifluoromethyl, alkylthio, arylthio, nitro, cyano, heterocycle or halogen atoms, and these substituents may connect with each other to form a ring.
The benzil- or benzoin-based compound used as a starting material is a compound having R.sup.1 and R.sup.2 which corresponds to the above formula (I) and is represented by the formula (II): ##STR5## wherein X is C.dbd.O in the case of the benzil-based compound or CHOH in the case of the benzoin-based compound.
Representative examples of the group, heterocycle and atoms which can be used as the substituents in the above R.sup.1 and R.sup.2 include alkyl group such as methyl, ethyl, butyl, pentyl and hexyl; cycloalkyl groups such as cyclopentyl and cyclohexyl; non-substituted or substituted aryl groups such as phenyl and p-nitrophenyl; alkoxy groups such as methoxy, ethoxy and butoxy; phenoxy; hydroxy; alkylamino groups such as dimethylamino, diethylamino and dibutylamino; arylamino groups such as diphenylamino and ditolylamino; trifluoromethyl; alkylthio groups such as methylthio, ethylthio and butylthio; arylthio groups such as phenylthio and tolylthio; nitro; cyano; heterocycles such as ##STR6## and halogen atoms such as fluorine, chlorine, bromine and iodine. Representative examples of the ring which is formed by connecting

REFERENCES:
patent: 4806664 (1989-02-01), Schrott et al.
Kijitani et al., "Effect of substituents in the aryl moiety of bis(1,2-diaryl-1,2-ethylenedithiolato)-nickel on the quenching of singlet oxygen and the reaction with singlet oxygen", Nippon Chemical Journal, vol. 1985, No. 3, pp. 433-437 (1985).
Chemical Abstracts, vol. 92, No. 16 (1980), Abstract No. 139914u.

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