STUDIES OF CONJUGATED SYSTEMS. XI. THE OXIDATION OF CIS-PHENYLBUTADIENE BY MEANS OF PERBENZOIC ACID¹

Abstract

Perbenzoic and peracetic acids have been used for some time to determine the degree of unsaturation and the rate of oxidation of olefinic compounds.2 Of particular interest in our investigations is the work of Bóeseken and Blumberger on the three isomeric phenylbutenes, 1,2-C6H6-CH=CH-CH2-CH3; A2'3-C6H6-CH2-CH=CH-CH3; 3,4-C6H5-CH2-CH2-CH=CH2; and also on cinnamic acid and its methyl

Organic Peracids.

“…Although considerable evidence has been collected that the reaction proceeds as shown in the equation, some workers (376,511) have suggested that the peracid adds directly to the double bond, followed by splitting out of benzoic acid. This erroneous idea has found its way into a standard reference work on organic chemistry (2).…”

Measurement of Internal Double Bonds in Polymers by Per-benzoic Acid Addition

“…(10) Filachione, E. M., 'Lengel, J. H., and Fisher, C. H., Ibid., 37, 388 (1945). (11) Filachione, E. M., Lengel, J. H., and Fisher, C. H., J. Am.…”

“…The first study of perbenzoic acid addition to double bonds was made by Prileschajew (IS), but the usefulness of the reaction has been confined to the preparation of hydroxy benzoates (11,12) and epoxides (2). Other peracids-peracetic (16), percamphoric (10), and perphthalic (3)-have been used as addition reagents in syntheses.…”