The Degradation of Carboxylic Acid Salts by Means of Halogen the Hunsdieceerreaction Robert G
THE DEGRADATION OF CARBOXYLIC ACID SALTS BY MEANS OF HALOGEN THE HUNSDIECEERREACTION ROBERT G. JOHNSON Department of Chemistry, Xavier University, Cincinnati 7, Ohio AND ROBERT K. INGHAM Department of Chemistry, Ohio University, Athens, Ohio Received November 17, 1966 CONTENTS I. Introduction.. ...... 11. Synthetic applicatio A. Aliphatic halides B. Alicyclic halides. C. Aromatic halides D. Heterocyclic hali 111. Materials and methods ....................................... 248 IV. Mechanisms., ...... V. Related reactions. ....... ......................................... 259 VI. Summary.. ......... VII. References.. ................................................................. 263 VIII. Addendum. ........................... .. 268 I. INTRODUCTION The degradation of a carboxylic acid salt in anhydrous medium by means of halogen to a halide of one less carbon atom than the original acid can be ex- pressed by the equation: RCOOM + Xz -+ RX + COz + MX Largely because of the extensive contributions of the Hunsdieckers (96, 97, 98, 99, 100, 101, 102) to our knowledge of this reaction, many chemists refer to the reaction under discussion as the “Hunsdiecker reaction.” Others designate the reaction by the names “silver salt reaction” or “silver salt-halogen reac- tion.” It has been proposed (95) that the name “Borodine reaction” be used, in recognition of the discovery of the reaction by Borodine (33). The authors of a recent book (179) incorrectly name this reaction M the Simonini reaction. The reviewers favor the use of “Hunsdiecker reaction,” if a name is to be given to this reaction, because of the many instances of the use of this termi- nology already in the literature and because of the large amount of developmental work carried out by the Hunsdieckers. The often-used descriptive names are contraindicated by the fact that the reaction is successful with salts other than silver salts, halogens other than bromine can be used, and the reaction of salts 219 220 ROBERT G.
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