Structures of two alkaline autoxidation products of BHA, a widely used antioxidant

In order to confirm the structures of the autoxidation products of 2-tert-butyl-4-methoxyphenol (BHA), X-ray crystallographic analyses have been undertaken. One of the products was converted to a dibenzoate, which was subjected to the analysis to establish the structure as the O ⁶,O ⁷-dibenzoyl derivative of (1R*,2R*,6S*,7S*,9R*)-4,9-di-tert-butyl-6,7-dihydroxytricyclo5.2.2.0^{2, 6}]undec-4-ene-3,8,10-trione. Crystallographic analysis of the major isomer of the two isomeric products gave its structure as (E)-4-tert-butyl-2-(3-tert-butyl-4-oxocyclopent-2-en-1-ylidene)cyclopent-4-ene-1,3-dione, which also established the structure of the minor isomer as the corresponding (Z)-isomer.