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Metody syntezy sulfidów fenylowo-fluorometylowych

Banach Ł., Ochal Z.

Wiadomości Chemiczne

2010

[Z] 64, 11-12

983-994

Aromatic compounds containing halogenomethylsulfonyl or halogenomethylsulfanyl group are often biologically active as fungicides or herbicides [1–6]. Especially important plant protection agents are fluorine compounds [7–12]. Through to specific activity in living organisms, fluorine compounds found wide application. One of the reasons of high activity of these compounds is their high lipophilicity, which provides increase of solubility in lipides. Due to this fact absorption of fluorine compounds is easier and their transport in organism is faster what increase their efficiency [13–15]. In this paper the methods of synthesis of aromatic compounds containing fluoromethylsulfanyl group are described. Aryl-fluoromethyl sulfides can be easily transformed into sulfones by oxidation [16–18]. Methods of preparation of aryl-fluoromethyl sulfides can be divided into three groups: 1. Fluorination of methylsulfanyl group [19–31] 2. Substitution of chlorine atom into fluorine in phenyl-chloromethyl sulfides [32–34] 3. Fluoromethylation of phenylothiols [35, 36].

Tranformations of trichloromethyl-4-chlorophenyl sulfone into new compounds with potential pesticidal activity

Ochal Z., Ochal I., Banach Ł

Polish Journal of Applied Chemistry

2010

Vol. 54, nr 1-4

49-61

The synthesis of trichloromethylphenyl sulfone derivatives as new potential pesticides is reported. The title sulfone was obtained in the four-step synthesis, starting from 4-chlorobenzene. and it was chlorosulfonated, reduced to the sulfinyl salt, which was transformed with chloroform to 4-chlorophenyldichloromethylsuIfone and in the next step with natrium hypohalite to the tide compound. TrichIoromethyl-4-chlorophenyl sulfone was nitrated and then subjected to the S'NAT reaction with ammonia, amines, hydrazine and other nucleophiles to give 2-nitroaniline and 2-nitrophenylhydrazine derivatives. After reduction of the nitro group - o-phenylenediamine derivative was obtained which was transformed into benzimidazole derivatives and other cyclic compounds. Characteristic IR spectroscopic data and microelementarv analyses of the new' products are reported.