48e 



SCIENCE 



[Vol. LVI, No. 1452 



i. e., of the distances between aluminum atoms in 

 the solid, is favorable to decarboxylation and 

 unfavorable to alkene formation. 



On the synthesis of thiazoUdine and thiasane 

 derivatives: F. B. Dains, E. Q. Brewster, J. S. 

 Blair and W. C. Thompson. The present report 

 is part of a larger investigation. The immediate 

 object of this part of the work was to devise 

 methods for the synthesis of thiazolidine and 

 thiazane derivatives of known structure. This 

 was accomplished as follows: (1) The addition 

 of mustard oils, ENCS, to aryl-allylamines, 

 ENHCsHg, formed diaryl-aUyl-thioureas, which 

 by the action of acids were converted to 2-aryl- 

 imino-3-aryI-5-methyl thiazolidines. (2) Aryl-N- 

 ethanols, ENHCH2CH2OH, gave with arylisothio- 

 cyanates and cyanates ureas which condensed 

 easily to thiazolidines and oxazolidines. (3) 

 From aryl-N-propanols and mustard oils 

 were obtained thioureas and then thiazanes, 

 SC(NE)NECH2CH2CH2. (4) Alpha-arylamino- 

 beta-hydroxl-gamma-chloro-propane combined with 

 aryl mustard oils to give 5-hydroxythiazanes. 



Urethanes from chlorine-substituted secondary 

 and tertiary alcohols: Lester Yoder. Certain 

 tertiary alcohols, for example, triehlorotertiary 

 butyl alcohol, which do not react directly with 

 phosgene, give the chlorooarbonates when the 

 dilute solution in benzene is treated with sodium 

 and then with phosgene. The products react 

 readily with ammonia and with aniline chloral 

 condenses with glycerol to form a substituted 

 1, 3-dioxole. The readiness with which this 

 product reacts with phosgene indicates a primary 

 rather than a secondary hydroxy!, hence the as- 

 sumption of a five-membered rather than a six- 

 membered ring. This dioxole derivative and 

 some of the chlorine substituted urethanes pre- 

 pared were found to have hj^pnotie properties. 



Gamma-chloropropyl urethanes and a synthesis 

 of the 1, S-oxazine ring : Arthitk W. Dos and 

 Lester Yoder. Gamma-chloropropyl alcohol re- 

 acts readily with phosgene to form a chlorocar- 

 bonate, and the latter reacts ammonia and with 

 aniline to form the carbamate and the carbanilate 

 respectively. Eemoval of hydrochloric acid from 

 gamma-chloropropyl carbanilate results in the 

 formation of the six-membered 1, 3-oxazine ring. 

 This reaction is analogous to that studied by Otto 

 and by Johnson and Langley in which the beta- 

 halogen alkyl carbanilates lose hydrochloric acid 

 and form the five-membered 1, 3-oxazole ring. 



Kemoval of iodine from aromatic iodo com- 

 pounds, and its bearing on electromerism : Ben 

 H. NicoLET and Eeuben B. Sandin. Several new 

 derivatives of 2-iodo-4-aminotoluene are described. 



With stannous chloride and hydrochloric acid, 

 iodine is removed from m-iodoamino derivatives, 

 as well as from o-iodoamino compounds; but the 

 rate of removal is some hundreds of times slower. 

 • The results are explained on the basis of a one- 

 sided reaction taking place on a mixture of elec- 

 tromers. The behavior of such a mixture is dis- 

 cussed. 



The spontaneous decomposition of unsaturated 

 aliphatic iodochlorides : L. B. Howell. Previous 

 work (J. A. C. S., 42, 997-9) upon iodoehloride- 

 1, 2-dichloro-2-iodoethylene and iodoohloride-2- 

 chloroethylene has shown that their spontaneous 

 decompositiion is not accompanied by loss of 

 chlorine (cf. Ann. 369, 135). Further investiga- 

 tion has shown that the expected shift of the 2 CI 

 atoms from the group — ICI2 to the double bond 

 is not the only change involved. Thus, when 

 CHCl = CHICI2 decomposes the products include 

 H I CI and C H CI as well as C H CI I (in 



2222 224 223^ 



addition to iodine monochloride and free iodine). 

 Evidently' either iodine chloride or chlorine may 

 add to the residue — CHCL — CHCL — or iodine 

 may be entirely replaced and the residue chlo- 

 rinated. The compound Cl2lCCl=CClI upon de- 

 composition gives C^Cl.,1,, C ClI and what is ap- 

 parently a constant boiling mixture of CaClg and 

 C2CI3I. Constants for the new halo-ethanes and 

 ethenes have been determined. 



The chlorination of S-amino-p-oymene : A. S. 

 Wheeler and J. V. Giles. p-Cymene was ob- 

 tained from spruce turpentine. It was nitrated 

 at 0° and reduced. The acetyl derivative was 

 chlorinated at room temperature in carbon tetra- 

 chloride solution. The product contains one 

 chlorine. This is in position 5 as shown by its 

 conversion into 2, 5-dichloro-terephthalio acid. 

 Salts of the ehloro aminoeymene were prepared. 

 By diazo reaction a new ehloro carvacrol was pre- 

 pared. The amino group was also replaced by 

 the carboxyl group, yielding a new benzoic acid. 

 A new series of dyes was prepared by coupling 

 with the following: phenol, resorcinol, salicylic 

 acid, alpha naphthol, beta naphthol, naphthol-2- 

 sulfonic acid, l-naphthol-4-sulfonic acid, 2-naph- 

 thol-7-sulfonie acid. A variety of colors was ob- 

 tained, some of great brilliancy. The amino 

 chlorocymene was also coupled with itself, form- 

 ing a neutral compound. By oxidation a new 

 cuminic acid was obtained. 



The catblytic preparation of divinylacetylene : 

 J. A. NiEUWLAND. Acetylene is passed into a 

 solution of cuprous chloride (three parts), am- 

 monius chloride (one part) and water (one part). 

 The absorption takes place indefinitely, and when 

 subsequently distilled, a mixture of oils comes 



