1914] Clarence J. West 257 



which melts at 108-9°. ^ith nitrous acid it gives methyl-ethyl 

 maleinic-imide oxime, melting at 20 1 ° . This has been considered by 

 Piloty and Stock^^ to be a mixture. This Compound was later 

 named kryptopyrrole^^ It has been synthesized by Knorr and Hess.^^ 

 A second base, isohemopyrrole, was isolated in a pure state, 

 which melts at 16-7°, bu_i2, 88°; the picrate melts at 119°; with 

 nitrous acid, isohemopyrrole gives the second oxime of methyl-ethyl 

 maleinic imide, melting at 219°. The styphnate forms yellow prisms, 

 melting at 136°. 



Me— C C— Et Me— C C-Et Me— C C— Et 



II II II II II II 



Me— Cv yCH HCs^ xC— Me Me— C\/C— Me 



N N N 



H H H 



Isohemopyrrole Kryptopyrrole Phyllopyrrole 



The third base, phyllopyrrole, is the most interesting. This has 

 been prepared synthetically by Fischer"*^ and its Constitution estab- 

 lished. It melts at 66-67°. The picrate, which is the most easily 

 soluble of the three, melts at 95°. It does not show the dimethyl 

 amino benzaldehyde reaction"*^ nor the pine-stick reaction. It is 

 not precipitated by aqueous mercuric chloride. That it is a pyrrole 

 is indicated by the fact that it may be reduced to a tetrahydro-base. 

 It forms a potassium salt with the evolution of hydrogen. 



Of the Chlorophyll derivatives investigated, phylloporphyrin 

 gives the largest yield of volatile reduction-product because it con- 

 tains only one carboxyl. Concerning the role of the four nitrogen- 

 containing nuclei of phylloporphyrine in reduction and oxidation, 

 the f ollowing may be stated : Two nuclei give, upon reduction, tri- 

 substituted pyrroles. They are the same as those which give methyl- 



•*! Piloty and Stock: Ann. d. Chem., 392, 215 (1912) ; Ber. d. deutsch, ehem. 

 Gesellsch., 46, 1008 (1913). 



■*2 Fischer and Bartholomäus : Ber. d. deutsch, chem. Gesellsch., 45, 1979 

 (1912). 



42 Knorr and Hess: Ber. d. deutsch, chem. Gesellsch., 44, 2578 (1911). 



** Fischer and Bartholomäus: Ber. d. deutsch, ehem. Gesellsch., 45, 466 

 (1912) ; Zeitschr. f. physiol. Chem., 77, 185 (1912) ; cf. Colacicchi : Atti R. Accad. 

 dei Lincei, 21 (I), 489, 653 (1912). 



45 Ehrlich: Die med. Woche, 1901, 151; Neubauer: Verhandl. d. Gesellsch. d. 

 Naturf. u. Arzte, 2, 68 (1903). 



