262 



SULPHUR COMPOUNDS 



[171-172. 



albin (Robiquet and Boutron-Charlard, 

 Journ. Pharm. [2] 17, 279 ; Will and 

 Laubenheimer, Ann. 199, 150; Gada- 

 mer, Arch. Pharm. 235, 83 ; Ber. 30, 



SYNTHETICAL PROCESSES. 



[A.] From toluene [54] and carbon 

 disulphide [160]. Paranitrobenzyl 

 chloride (see under p-hydroxybenzoic 

 aldehyde [119 ; E]) is converted into 

 a phthalimide derivative (see under 

 benzoic aldehyde [114 ; j]) by inter- 

 action with potassium phthalimide (Ga- 

 briel, Ber. 20, 2224), and this deriva- 

 tive converted into p-nitrobenzylamine 

 by heating with hydrochloric acid at 



190-200. The nitro-amine gives p- 

 aminobenzylamine on reduction, and 

 the latter p-hydroxybenzylamine by 

 the diazo-method. The mustard oil is 

 obtained from the base by the usual 

 method (Salkowski, Ber. 22, 2143). 



p-Nitrobenzylamine can also be ob- 

 tained from benzylamine (see under 

 benzyl mustard oil [169 ; A to end]) 

 by acetylation, nitration of the benzyl- 

 acetamide, and reduction of the p-nitro- 

 derivative (Amsel and Hofmann, Ber. 

 19, 1284). The generators of benzyl- 

 amine, viz. lenzoic acid and acetic alde- 

 liyde } hippuric and pkenylacetic acids, 

 and styrene, thus become, with carbon 

 disulphide, generators of p-hydroxy- 

 benzyl mustard oil. 



CYANOGEN COMPOUNDS. 



172. Hydrogen Cyanide ; 



Hydrocyanic or Cyanhydric Acid ; 



Prussic Acid ; Formonitrile. 



H.CN 



NATURAL SOURCES. 



Occurs to a considerable extent in 

 the free state or in very loose combina- 

 tion in all parts of Pangium edule, Java 

 (Greshoff, Ber. 23, 3549). Also in 

 Hydnocarpus iuebrians = If. wigfitiana ? 

 and //. alpinus (Ibid. 3550). The sweet 

 and bitter cassava contain hydrogen 

 cyanide, especially the skin (Francis, 

 ' Analyst/ 2, 4 ; Carmody, ' Bulletin of 

 Miscellaneous Information/ Trinidad; 

 'Nature/ 63, 500 : for occurrence of 

 hydrogen cyanide in Pangium edule and 

 in bitter almonds see also Marco Soave, 

 Journ. Ch. Soc. 80, II, Abst. 332). 



The hydrogen cyanide complex is 

 contained in the glucoside amygdalin 

 (for occurrence see under benzoic alde- 

 hyde [114]). The complex exists in 

 plants belonging to the Amygdalacese, 

 Asclepiads, Bixacea3, Tiliacese, Sapo- 

 tacese, Sapindacea?, Papilionacese, Con- 

 volvulacese, Euphorbiacese, Linacere, 

 and Aroidese (Greshoff). Traces of 



free hydrogen cyanide have been found 

 among Saxifrages, in young shoots of 

 certain species of Ribes, viz. R. rubrum, 

 R. nigrum, and R. anreum. The seed 

 embryo of Eriobotyra japonica contains 

 04 per cent, of hydrogen cyanide. 



The complex exists in a compound 

 occurring in many wild Rosacese and in 

 an amygdalin-like compound found in 

 the young green parts of the Ranuncu- 

 laceous Aquilegia vulgaris. No hydro- 

 gen cyanide could be found in the 

 Aroidese, Arum maculatum, A. ilalicum, 

 Arisarum vulgar e t Amorphophallas rivieri, 

 or Dieffenbackia seguine (Hebert, Bull. 

 Soc. [3] 17, 664; 19, 310). R. Fischer, 

 contrary to the statement of Greshoff, 

 was unable to find hydrogen cyanide 

 in Mitchella repens (Pharm. Rev. 16, 

 98). 



Amygdalin, or some glucoside yield- 

 ing hydrogen cyanide on hydrolysis, is 

 present in the leaves of Indigqfera gale- 

 go'ides (Van Romburgh, SchimmePs Ber. 

 Oct. 1894; April, 1896). 



The distribution of hydrogen cyanide 

 in various parts of Prunus laurocerasus 

 has been investigated by Van der 

 Ven (Ch. Centr. 1898, 2, 678). 

 The opening buds of Primus lauro- 



