ORGANIC CHEMISTRY 545 



attached to the i or s carbon atoms, as 2:5-diphenylthiophen-3- 

 mercurichloride [iii] readily yields 3-mercury-di-2:5-diphenyl- 

 thiophen. 



[iii] 



White (/. Amer. Chem. Soc, 1920, 42, 2355) has described 

 a number of mercury derivatives of the phthaleins. The 

 mercury enters in the ortho position to the hydroxyl group 

 when this is free, and may be introduced by the action of yellow 

 mercuric oxide on a solution of the phthalein salt, when phtha- 

 lein mercurihydroxides are formed, or by means of mercuric 

 acetate, which gives acetoxymercury derivatives, or a mixture 

 of these with the hydroxides owing to partial hydrolysis. 

 Hart and Hirschfelder (/. Amer. Chem. Soc, 1920, 42, 2678) 

 have obtained mercurihydroxides from phenylcarbinols such as 

 saligenin and m-nitro-/)-hydroxybenzyl alcohol. These have 

 an antiseptic action of the order of mercuric chloride, but are 

 far less irritant. 



Whitmore and Middleton (/. Amer. Chem. Soc, 1921, 43, 

 619) have found that mercuric acetate reacts with excess of 

 phenol in the absence of a solvent to form the 0- and p- mer- 

 curiacetates, the disubstituted product not being produced as 

 in aqueous solution. The phenol-mercurichlorides, on boiling 

 with a solution of potassium iodide, are decomposed, giving 

 phenol, mercuric iodide, and potassium hydroxide ; potassium 

 bromide is less effective, while the chloride is without action. 

 When, however, the phenolic hydroxyl group is acetylated, this 

 reaction does not take place, the mercuriiodide being formed, 

 together with a small amount of the mercury diphenyl de- 

 rivative. The action of haloid salts in eliminating mercury 

 from organo-mercury compounds is not common where the 

 Hg-C linkage is concerned, particularly in the aromatic series, 

 although a few cases have been reported. This reaction is of 

 considerable importance in connection with the therapeutic 

 use of these compounds. 



Other papers are those of Vecchiotti {Gazzetta, 1921, 51, 

 ii, 208) on the position of the mercury group in ^-toluidine- 

 mercuriacetate ; Oliveri-Mandal^ {Gazzetta, 1921, 51, i, 125) 

 on derivatives from antipyrine and pyramidone ; Paolini 

 {Gazzetta, 1921, 51, ii, 188) on mercuriacetates of thymol, 

 phenol, ^-naphthol and vanillin ; Tiffeneau and Gannage 



