OCTOBEE 27, 1922] 



SCIENCE 



487 



over. The one which distills over at 54° C. is 

 presumably vinylaeetylene of the formula, 

 CH2=CH— Cz=CH. Between 75° and 95° a 

 highly refractive oil, of formula CgHe, supposed 

 to be divinylaeetylene, comes over. About one 

 kilo of the above liquid is used in each flask. 

 After repeated distillations the mixture continues 

 to absorb the gas even for years without deteriora- 

 tion of the catalyst. About SO to 110 g. of 

 product are obtained at each distillation. The 

 divinylacet3'lene forms stable tetra and octobro- 

 mides which crystallize well from alcohol and 

 have definite melting points. When allowed to 

 stand even in sealed tubes the oil slowly changes 

 to a gel and finally to a solid which is extremely 

 explosive. If the original substance is put back 

 into the copper mixture mentioned above it can 

 be kept indefinitely for use when needed b}' dis- 

 tilling it oif at a temperature not exceeding 13° 

 C. When cupric chloride is added to the mixture 

 dichloroethylene is formed, an4 no hydrocarbons 



The application of the Friedel and Craft reac 

 tion to non-'benscnoid compounds: James F, 

 NoERis and Eam Pkasad. Continuation of pre^ 

 vious work showed that benzoyl chloride con 

 denses, under the influence of aluminium chloride, 

 with ethylene, propylene, butylene, isobutylene, 

 trimethylethylene and isopropylethylene. The 

 product of the reaction in each case was the un- 

 saturated ketone formed as the result of the re- 

 placement of one hydrogen atom in the hydro- 

 carbon by a benzoyl group. Hydrogen chloride 

 addition products of the unsaturated ketones were 

 also formed. Condensation was also effected be- 

 tween benzoyl chloride and malonic ester and 

 diisopropyl. The study of the application of the 

 reaction to saturated hydrocarbons is being con- 

 tinued. 



Some condensations with olefines. A contriiu- 

 tion to our Icnowledge of the Friedel-Craft reac- 

 tion: 0. E. BooRD and E. S. Hanson. 

 Olefines condense in the presence of anhydrous 

 aluminum or ferric chloride to form oily addition 

 products. These addition products are verj^ re- 

 active, undergoing the following series of trans- 

 formation: (1) With benzene they form inter- 

 mediate condensation products which upon hy- 

 drolysis yield alkyl .benzenes; (2) with phenol 

 they form intermediate condensation products 

 which upon hydrolysis yield alkyl phenols; (3) 

 by direct hydrolysis by cold concentrated hydro- 

 chloric acid they yield alkyl chlorides; (4) with 

 acetyl chloride they yield chloro and unsaturated 

 ketones. Ethylene, butylene and amylene give 

 similar results. A scheme of reactions is given 



as a simple explanation of the above reactions as 

 well as of the Friedel-Craft synthesis of hydro- 

 carbons. The explanation offered agrees per- 

 fectly with that given by Steele for the formation 

 of aromatic ketones by the Friedel-Craft reaction. 



The action of titanium tetrachloride upon cer- 

 tain organic compounds: Joseph F. Haskins and 

 William McPhekson. The work described in 

 this paper is the outgrowth of an attempt to pre- 

 pare an optically active compound of titanium. 

 In the course of this work it was found necessary 

 to study more in detail the fundamental reactions 

 between titanium tetrachloride and representatives 

 of the important groups of organic compounds. 

 The paper gives the results of some of these ex- 

 periments. Among other reactions, it was found 

 that titanium tetrachloride could be substituted 

 for aluminum chloride with advantage in the 

 synthesis of certain compounds by the Friedel- 

 Craft reaction. For example, benzoyl chloride 

 and benzene in the presence of titanium tetra- 

 chloride react to give benzophenone a reaction 

 which serves as a good laboratory method for 

 preparing this substance. The work is being con- 

 tinued. 



A comparison of ferric and aluminum chlorides 

 in their action on chloral, hroinal and organic 

 compounds: G. B. Prankforteb and E. E. Hab- 

 Eis. A continuation of the work of Frankforter 

 and Kritchevsky. The two chlorides have been 

 compared in their condensing properties, using 

 chloral and bromal with the phenolic ethers and 

 other organic compounds. Among the most im- 

 portant compounds prepared are the following: 

 Diphenetyltribromoethane, tetrabromodiphenetyl- 

 tetrabromoethane, diphenetyldibromoethylene, di- 

 phenetyldiethoxythylene, diphenetyldiacetoaeetyl- 

 ethylene, dibromophenetyldibromoethylene, tetra- 

 phenetyldimethylacetylene. The properties of 

 these compounds have been carefully worked out 

 in addition to the comparison of the action of the 

 two chlorides in their preparation. 



Optically active dyes: A. W. Ingersoll and 

 KoGER Adams. A study of the action of opti- 

 cally active dyes on fibers should throw light on 

 the mechanism of dyeing. The preliminary work 

 of which this is a report has involved the study 

 of an easy method for preparing pairs of active 

 dyes. An extremely convenient way has been 

 found by first synthesizing and resolving into 

 optically active isomers certain amino acids, in 

 particular phenyl amino acetic acid. These 

 amino acids can be converted into dyes by the 

 following general reactions which take place very 

 satisfactorily in the laboratory : 



