474 



SCIENCE 



[N. S. Vol. LIV. No. 1402 



namely, /3-isatin derivatives from isatin itself, and 

 a-derivatives from the a-chloride. 



These neiv products are all highly colored, and, 

 in their molecular configuration, resemble the 

 dyes of the indigoid group. The color of a-de- 

 rivatives, which contain the true indigoid ehromo- 

 phore, 



A 



=0 ysB^ 



\y 



as postulated by Olaasz, is deeper than that of 

 the corresponding ;8-homologues. 



Synthesis of the soporific nirvanol (4, 4-phenyl 

 ethyl hydantoin) : William T. Bead. Nirvanol (4, 

 4-phenyl ethyl hydantoin), a soporific now exten- 

 sively used in Europe, has been made in good 

 yield by the following method. Phenyl ethyl ke- 

 tone, prepared from propionyl chloride and ben- 

 zene by the Friedel and Crafts reaction, is con- 

 densed with ammonium cyanide in alcohol solu- 

 tion. 

 C,H5C00,Hj + NH.CN -^ CeH5(CA)C(CN)NH,. 



The resulting a-phenyl a-aminobutyronitrile, or its 

 hydrochloride, is treated with potassium cyanate 

 in glacial acetic acid solution, whereby phenyl 

 ethyl hydantoic nitrUe is obtained. The nitrile is 

 readily converted into 4, 4-phenyl ethyl hydantoin 

 by boiling with h3'drochloric acid. 



Ofi^sC CgHg )C[aS )IIHC013H2 



RH 

 I 



CO 



I 



HH. 



\ 



°2H6 



The synthesis of ^-chJorallylchloride from a, 7- 

 dichlorhydrin: Arthur J. Hill and Edwin J. 

 Fischer. A practical method for preparing chlo- 

 rallylohloride is not described in the chemical lit- 

 erature. A method has now been developed for 

 the practical preparation of this chloride from 

 dichlorhydrin by dehydration of the latter with 

 phosphorus oxychloride. This chloride is of im- 

 mediate interest and value 



OlCHj . CHOH . CH.Cl -^ CICH : CH . CH,C1 



for the synthesis of new organic combinations of 

 therapeutic and pharmacological interest. 



The action of ferrous hydroxide-peroxide on 

 thymine, lactic acid and alanine: Oskar Bau- 



DISCH. Ferrous hydroxide-peroxide acts in a 

 double capacity as an oxidizing and a reducing 

 agent. From a biochemical standpoint it be- 

 haves lite an enzyme. As a chemical reagent it 

 has received hitherto very limited attention, but 

 its marked activity at ordinary temperature due 

 to the presence of iron in its molecule stimulates a 

 special interest in a study of its action on bio- 

 chemical products. 



The behavior of cystine to acid hydro'ysis: 

 Walter F. Hoffman and Eoss Aiken Gortnek. 

 Many authors agree that the amino acid, cystine, 

 is destroyed by acid hydrolysis but no decompo- 

 sition products have been isolated. In the present 

 study a large quantity of cystine was boiled with 

 20 per cent, hydrochloric acid for 196 hours, ali- 

 quots being removed at intervals of 3, 6, 1'2, 24, 

 48, 96, 144, and 196 hrs. Various possible chem- 

 ical changes were followed throughout this pe- 

 riod. The authors find that (1) decarboxyliza- 

 tion and deamination proceed very slowly, (2) 

 that the sulfur is not markedly broken off by 

 boiling, and (3) that the major change is the 

 alteration of the cystine molecule into an "iso- 

 meric ' ' cystine with different crystal form and 

 different solubOities, which forms different deriva- 

 tives from ordinary cystine. Approximately 90 

 per cent, of the original cystine was isolated as 

 "isomeric" cystine after boiling for 196 hrs. 



A comparison of certain derivatives of "pro- 

 tein" cystine and the "isomeric" cystine formed 

 iy acid hydrolysis: Eoss Aiken Gortner and 

 Walter F. Hoffman. Certain derivatives of 

 the "isomeric" cystine noted in the preceding 

 paper were compared with the corresponding de- 

 rivatives of the natural 1. cystine. Protein cys- 

 tine crystallizes in large hexagonal plates, the 

 isomeric cystine iu tiny microscopic prisms. The 

 benzoyl derivative of 1. cystine crystallizes in 

 needles, m. p. 180^181". The "isomeric" ben- 

 zoyl derivative crystallizes in diamond-shaped crys- 

 tals, m. p. 168°. The phenyl isocyanates melt at 

 148-149° and (isomeric) 181°, respectively. It 

 was found impossible to prepare a phenyl hydan- 

 toin from the phenyl isoeyanate of the isomeric 

 cystine, whereas a phenyl hydantoin melting at 

 122-123° was easily prepared from the corre- 

 sponding derivative of the normal 1. cystine. 

 The cysteio acids were prepared and show dif- 

 ferent properties and different erj'stal form. The 

 study is being continued. 



Charles L. Parsons 

 Secretary 



