On the induced oxidation of iodobenzene during the oxidation of benzaldehyde in an atmposphere of oxygen

Abstract

This investigation is an attempt to use benzaldehyde and oxygen instead of perbenzoic acid as an oxidising agent. 1.In a series of papers 1) J. B o e s e k e n and several of his pupils have published the results of their researches on the oxidation of organic compounds by means of peracetic acid and perbenzoic acid.Especially those ohtained by the action of the latter substance drew our attention as one of u s * ) has studied some induced oxidations observed during the oxidation of benzaldehyde in an atmosphere of oxygen or air.Moreover, in collaboration with P. A. A. v a n d e r B e e k, he showed 3) that a solution of benzaldehyde in acetone (and some other solvents) produces, on oxidation in oxygen, perbenzoic acid in good yield (up to 63 %), especially in direct sunlight. In this connection the question arose whether some of the reactions observed by B o e s e k e n with perbenzoic acid could be obtained also by the action of oxidizing benzaldehyde. The oxidation of I ) J. B 6 e s e k e n and c:ollaborators: (1931); Chem. Weekblad 31, 166 (1934); and the dissertations of W. C. Smi t, C. v a n M e e u w e n (19.34). J. S t u u r m a n (1936) and J. D. J a c o b s (1936). 2, W. P. J o r i s s e n , Z. physik. Chem. 22, 34, 54 (1897); W. P. J o r i s s e n and W. E. R i n g e r , J. prakt. Chem. (2) 72, 173 (1905); W. P. J o r i s s e n and P. A. A. v a n d e r B e e k , Rec. trav. chim. 45, 245 (1926Rec. trav. chim. 45, 245 ( ), 46, 42 (1927Rec. trav. chim. 45, 245 ( ), t9, 138 (1930; P. A. A. v a n d e r B e e k . Ibid. 47, 301 (1928); A. H. B e l i n f a n t e , dissertation Leiden 1933. W. P. J o r i s s e n and P. A. A. v a n d e r B e e k.. Rec. trav. chim. 45, 245 (1926); P. A. A. v a n d e r B e e k, dissertation Leiden 1926, Rec. trav. chim. 47, 286 (1928.

Organic Peracids.

“…Jorissen and Dekking studied the oxidation of iodobenzene dissolved in acetaldehyde (277) or in benzaldehyde (276) through which oxygen was being passed. Peracetic or perbenzoic acid (prepared and utilized in situ) was assumed to be the oxidizing agent.…”