6 Journal of the Mitchell Society \_JuJy 



Allen, W. M.; Balcomb, E. E.; *Brimley, C. S. ; Brimley, H. H 

 Bruner, S. C; Cain, William; *Carruth, F. E.; Clapp, S. C; *Cobb, 

 Collier; Cobb, Wm. B.; Coker, W. C; Collett, R. W. ; *Cunningham 

 Bert ; Dixon, A. A. ; Downing, J. S. ; Edwards, C. W. ; *Farmer, C 

 M.; *Field, R. H. ; Fulton. H. R. ; Geiser, S. W. ; *George, W. C. 

 Gove. Anna M.; *Gudger, E. W.; Hammel, W. C. A.; Harding, W, 

 T.; Herty, C. H.; *Hickerson, T. F. ; Hobbs, A. Wilson; Hoffman 

 S. W.; Holmes, J. S. ; Hutt, W. N. ; Ives, J. D. ; Kilgore, B. W. 

 *Lanneau, J. F. ; Lay, George W. ; *Leiby, R. W. ; Lewis, R. H. 

 Lyon, Mary; Mclver, Mrs. Chas. D. ; MacNider, W. deB. ; Mac- 

 Nider, G. M.; Markham, C. B.; Mendenhall, Gertrude, W. ; *Metcalf, 

 Z. P.; *Miller, E. T.; Mills, J. E. ; Newman, C. L. ; *Patterson, 

 A. H. ; Pegram, W. H.; *Plummer, J. K. ; *Poteat, W. L. ; Potwine, 

 Elizabeth B. ; Pratt, J. H. ; Ragsdale, Virginia ; Randolph, E. 

 Oscar; Rankin, W. S. ; Robinson, Mary; *Sherman, Franklin, Jr.; 

 Shore, C. A.; Smith, J. E. ; *Spencer, H.; Stiles, C. W.; Strong, Cora; 

 *Totten, Henry R. ; Venable, F. P. ; *Wheeler, A. S. ; Williams, L. F. ; 

 W^ilson. H. V. ; Wilson, R. N. ; *Withers, W. A. ; *Wolfe, J. J. 



The following papers were presented : 

 DESMOTROPY 



ALVIX S. WHEELER 



The first case of keto-enol isomerism among the phenols of the 

 naphthalene series was recently reported by Willsaetter and Wheeler. 

 Juglone, a dyestuff in green walnut shells, yields on reduction 1, 4, 8- 

 trihydroxynaphthalene, melting at 152°. After once being melted, it 

 melts thereafter at 96°. Since this type of compounds is very sensitive 

 to alkalies, weakl}' basic reagents as semicarbazine and phenylsemi- 

 carbazine were emploj-ed to detect the carbonyl group. The lower 

 melting product was found to be the ketonic form. Some work, not 

 yet published, on 1, 4, 5, 6-tetrahydroxynaphthalene reveals another 

 case of this nature. Here however it has been impossible to separate 

 the two forms, the compound melting at 154° responding readily to both 

 enolic and ketonic reactions. Numerous isomerisation methods fail to 

 reveal another form. The application of Knorr's ferric chloride method 

 and Kurt Meyer's bromine method to approximate the relative amounts 

 of the isomers present is not practicable to the above cases. Ferric 

 chloride oxidizes the compounds to quinones wliile bromine enters the 

 ring of either form. 



