152 Report of Schimmel $ Co. April 1913. 



of the bodies thus obtained, in particular towards enzymes, with the natural glucosides 

 of mustard oil. It has long been known that aromatic sulpho-urethanes, as for instance 

 phenyl sulpho-urethane, (II) are pronounced acids, inasmuch as they react in the sense 

 of their tautomeric, acid, form (III). Accordingly, with heavy metals, they yield stable 

 salts from which ethers alkylised with sulphur are obtained (IV). 



In view of the fact that, so far, purely aromatic isosulphocyanates have not been 

 observed in nature it was interesting to determine whether sulpho-urethanes aliphatically 

 substituted in nitrogen could be converted by an analogous method into esters of 

 iminothiol carbonic acid. With this object in view Schneider took as his starting 

 point allyl sulpho-urethane, which is generated from allyl isosulphocyanate and an excess 

 of alcohol, b. p. 115 to 118° at 14 mm. In contradistinction to its aromatic analogues, 

 this body does not perceptibly dissolve in aqueous alkalies, but with ammoniacal 

 silver solution it yields a fairly stable silver salt (V) in which according to all appearance 

 the silver is in combination with sulphur. This salt, when heated with ethyl iodide 

 in a sealed tube, is converted into the allyl sulpho-urethane ethylether, allylimino thiol 

 diethyl carbonate (VI). When boiled with an alkaline solution of lead oxide this body 

 remains stable, in contradistinction to sulpho-urethane, which immediately forms sulphide 

 of lead. Furthermore, when heated with sulphuric acid, it splits off mercaptane, hence 

 the newly-introduced ethyl is certainly combined with the sulphur and not with the 

 nitrogen. Schneider hopes, later on, to be able to report on the behaviour of the 

 synthetic ester towards silver nitrate and enzymes. 



C 3 H r) N:C< S - C ° H "°* 

 X)S0 2 OK 



(I) Sinigrine. 



C 6 H 5 • NH • CS (OC 2 H fi ) < > C 6 H 5 ■ "M : C (SH) (OC 2 H 5 ) 



•(II) Phenylsulpho-urethane. (Ill) Tautomeride. 



(iv) C 6 H 6 N : C(SAg)(OC 2 H 5 ) + CH 3 ) = C 6 H 5 -N : C(SCH 3 )(OC 2 H 5 ) + AgJ 



Silver salt of phenylsulpho-urethane. Ether alkylised with sulphur. 



(V) C3H5N : (CSAg)(OC 2 H B ) (VI) CsH 6 -N : C(SC 2 H 5 )(OC 2 H 5 ) 



Silver salt of allylsulpho-urethane. Allyl iminothiol diethyl carbonate. 



A sulphone-mustard oil from the seed of Erysimum Perofskianum is described on 

 p. 52 of the present Report. 



Alkylidene hydrazines. On the present occasion we are again able to report 

 on the resolution of alkylidene hydrazines 1 ). Kishner 2 ), in continuing his previous 

 investigations, has found that when menthylidene hydrazine is heated in the presence 

 of pieces of platinized porous tile, menthane is formed: b. p. 171°, d^ 0,7963. Men- 

 thylidene hydrazine is obtained by heating menthone and hydrazine hydrate: b.p. 248 

 to 249°. By analogous method isothujylidene hydrazine is formed from thujone and 

 hydrazine hydrate. When «'sothujylidene-hydrazine is heated with potassium hydroxide, 

 the azine of ?"sothujane results; when boiled with 20 p. c. sulphuric acid ^sothujane is 



x ) Comp. Report April 1912, 195; October 1912, 165. — 2 ) Journ. russ. phys. chem. Ges. U (1912), 1754; 

 Chem. ZentralU. 1913, I. 706. 



