Phenylmercuric chloride, addition

A 94 per cent, yield may be obtained from mercury diphenyl under the following conditions 2-5 grams of the latter substance in 25 c.c. of acetone are treated with 1-95 grams of mercuric chloride in 10 c.c. of acetone, when phenylmercuric chloride (3-7 grams) is immediately precipitated. A further 0-5 gram may be recovered from the filtrate by the addition of water, A similar reaction takes place in alcohol. 

Qiloroform yields both the trichloromethyl anion and dichlorocarbene as reactive intermediates under basic phase transfer conditions. The trichloromethyl anion reacts with phenylmercuric chloride under these conditions to yield phenyl(trichloromethyl)-mercury (72%). The product is unstable, however, to the 50% aqueous sodium hydroxide solution usually used in phase transfer catalysis. When 10—15% aqueous sodium hydroxide solution was used, while maintaining the ionic strength by addition of potassium fluoride, the product survived. Reasonable yields of the mercury compound were thus obtained and the reaction was successfully extended to bromodichloromethane [yielding 64% of phenyl(bromodichloromethyl)mercury] and bromoform [yielding phenyl(tribromomethyl)mercury, 54%]. The transformation is illustrated in equation 3.18 [26]. 

The commercial production of mercury fungicides from organolead compounds is based on patents by Kharasch 184,185). The mercury compounds are used in the disinfection of seeds and grains. Typical compounds are ethylmercuric chloride, ethylmercuric sulfate, ethyl-mercuric phosphate, phenylmercuric acetate, and compounds derived from substituted phenols and ureas. The manufacture of these compounds was reviewed by Whelen in 1957 310>. The alkylation reaction is a general reaction, and a number of additional patents has been issued on methods similar to Whelen s. A representative equation is ... 

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