Ryan and O'Neill — Studies in the Diflavone Group. 183 



14. Dianisylidene-diflavanone. 

 /°\ ^ CH \ ^°\ 



CH-CH C*^ ^C CH CH 



6 5 1 | xni || I s5 



CHOCHCH=C. c^. C. X=CHCHOCH 



Two grammes of a-clibenzylidene-diacetoresorcinol and four cubic centi- 

 metres of anisaldehyde were dissolved in a mixture of chloroform and alcoho 

 saturated with anhydrous hydrochloric acid. On heating the solution to 

 gentle boiling for several hours under a reflux condenser, it turned a dark 

 brownish-red colour. When the solution was concentrated and mixed with 

 alcohol, about 27 grammes of yellow crystals separated. After two 

 recrystallizations from chloroform and alcohol the solid melted at 278-279° C. 

 and gave on analysis the following results : — 



01342 substance gave 0-3904 C0 2 and 0-0579 H 2 0, 

 corresponding to C 79-33, H 4-8, 

 C w H 30 O 6 requires C 79-21, H 4-95. 



JUianisylidene-diftavanone crystallizes in faint yellow rhombs, which are 

 scarcely soluble in alcohol, ether, or ligroin, soluble in benzene, and very 

 readily soluble in warm chloroform. 



When suspended in boiling alcohol, it gave no coloration with ferric 

 chloride. 



The crystals dissolve in concentrated sulphuric acid to a deep blue 

 solution, which changes to violet, and finally, after some time, becomes red. 



15. Dipiperonylidene-diflavanone. 

 /°\ ^- CH \ /-°\ 



CH-CH C**' (T CHCH 



a 6 M I XIV || | 6 = - 



CH 2 <0> C H 3 CHrC \ co /-H CH / C ^ co / C = CH( i H 3 < Q > CH 



In a manner similar to that described for dianisylidene-diflavanone we 

 obtained about 1-2 grammes of dipiperonylidene-diflavanone from 2 grammes 

 of a-dibenzylidene-diacetoresorcinol and a slight excess of piperonal. The 

 solid was recrystallized from pyridine and xylene, and washed with alcohol. 

 When dried at 110° C, it melted to a reddish liquid at 296° C, and gave on 

 analysis the following results : — 



0-1306 substance gave 0-3600 CO, and 0-0505 H,0 

 corresponding to C 75-18, H 4-29 

 C 40 H 26 8 requires C 75-68, H 4-12. 



K.I.A. PKOC, VOL. XXXII,, SECT. B, [2 D] 



