HILL AND CORNELISON. — CROTONOLACTONES. 5 



crotonolactone itself proved to be a matter of such difficulty that we 

 attempted to find some derivative which would be more manageable. 

 The bodies containing the aniline residue in place of one of the halo- 

 gen atoms were found to be useless for our purpose, since they were 

 decomposed by boiling in alkaline solution with the formation of 

 phenylisocyanide, and the phenylamidocrotonolactone formed from 

 them by reduction was also decomposed with the formation of aniline 

 under the same conditions. It seemed probable that the corresponding 

 derivatives containing the phenoxy group would prove to be much 

 more stable. AYhile we have not yet succeeded in replacing the bro- 

 mine of the body C 4 H 2 Br 2 2 directly by the phenoxy group, we have 

 had no difficulty in preparing such a body by the reduction of the 

 bromanhydride of the mucophenoxybromic acid which was described 

 by Hill and Stevens.* The body thus formed was easily shown to be 

 a phenoxybromcrotonolactone, since it dissolved in hot alkaline solu- 

 tions with the formation of the salts of the corresponding oxy-acid. 

 On acidifying the well cooled akaline solution the phenoxybromoxy- 

 crotonic acid was obtained, which was stable under ordinary conditions, 

 but which was again converted into the lactone by heat. These results 

 were fully confirmed by a study of the phenoxychlorcrotonolactone, 

 which was prepared by the reduction of mucophenoxychlorylbromide. 

 The position which the phenoxy group takes in entering mucobromic 

 acid has already been shown with sufficient precision by Hill and 

 Stevens, since a remarkably stable phenoxybromacrylic acid is readily 

 formed from this product by the action of alkalies. The phenoxylac- 

 tones containing halogen must therefore have the constitution 



BrC - CH 2 C1C - CH 2 



V 





o 



C fi H B OC - CO C.H^OC - CO 



and the analogous bodies containing halogen alone the structure 



BrC - CH„ C1C - CH 2 



X X 



BrC - CO C1C - CO 



The formation of these bodies from tribrom- and trichlorpyromucic 

 acids seems to us to be most readily explained by assuming that a tri- 

 substituted furfuran is first formed with the loss of carbonic dioxide : 



* These Proceedings, XIX. 262. 



