Acid Derivatives: Volume 2 (1979)

Chapter 12 Radiation chemistry of acids, esters, anhydrides, lactones and lactams (pages 755–780): O. I. Micic and O. S. Gal
Chapter thirteen The electrochemistry of carboxylic acids and derivatives: Cathodic discount rates (pages 781–824): James P. Coleman
Chapter 14 Decarbonylation reactions of acid halides and aldehydes through chlorotris?(triphenylphosphine)rhodium(i) (pages 825–857): M. C. Baird
Chapter 15 Pyrolysis of acids and their derivatives (pages 859–914): R. Taylor
Chapter sixteen Transcarboxylation reactions of salts of fragrant carboxylic acids (pages 915–944): Josef Ratusky
Chapter 17 Micellar results upon deacylation (pages 945–1020): C. A. Bunton and L. S. Romsted
Chapter 18 The chemistry of thio acid derivatives (pages 1021–1062): J. Voss
Chapter 19 The synthesis of lactones and lactams (pages 1063–1330): James F. Wolfe and Michael A. Ogliaruso

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It was shown that the proton reduction wave of boric acid in aqueous tetraethylammonium iodide was replaced by a bigger wave at less negative potentials as small amounts of salicylic acid were added. The size of the wave could not be accounted for by the separate components and was, therefore, ascribed t o the reduction of the hydrogen atom in a complex with a higher degree of dissociation than the original acids. However, no second wave due t o aldehyde formation was observed. Robertson and collaborators3 went further and prepared mono- and disalicylborate complexes by a known method3 * .

V. Madhaven. N. N. Lichtin and E. J. Org. , 41, 2320 (1976). 70. P. Neta,J. Phys. C h e m , 75,2570 (1971). 71. N. H. Anderson, A. J. Dobbs, D. J. Edge, R. 0. C. Norman and P. R. West, J. Clrem. (B), 1004 (1971). 72. 0. P. Chaula and R. W. Fessenden, J. Pliys. , 79,76 (1975). 73. P. Neta and R. W. Fessenden,J. Phys. , 77, 620 (1973). 74. J. Lilie and R. Fessenden, J. Phys. O i e m . , 77,674 (1973). 75. R. S. Alger, T. H. Anderson and L. A. Webb, J. a i e m . , 30,695 (1959). 76. Y. Nakajima, S.

In aqueous diglyme or dioxane propionic acid was formed, but in aqueous DMSO adipic acid was the major product8 (equation 42). The direct electrochemical version of this reaction has 2 CH2CHC02H Na-Hg DMSO-HzO ' H02C(CH2)4C02H (42) 70% apparently not been pursued, although a similar reaction was observed for cinnamic acida4. The electrohydrodimerization (EHD) reaction will be discussed in more detail for carboxylic esters. Numerous other examples of double-bond hydrogenation in a$-unsaturated acids have been given in Reference 6 (p.

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