Photolysis of 2,6 di-tert-butyl-4-tert-butylperoxy-4-methyl-2,5-cyclohexadienone
✍ Scribed by J. Pilaǎ; J. Kovářová; J. Pospíšil
- Publisher
- John Wiley and Sons
- Year
- 1980
- Tongue
- English
- Weight
- 355 KB
- Volume
- 14
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
Abstract
The photolysis of a heptane solution of 2,6‐di‐tert‐butyl‐4‐tert‐butylperoxy‐4‐methyl‐ 2,5‐cyclohexadienone (1) with light of 360–480 nm in the presence of 2,6‐di‐tert‐butyl‐4‐methylphenol or 2,4,6‐tri‐tert‐butylphenol gives rise to their corresponding phenoxyls in a reaction with the tert‐butoxyl arising in the photolysis. Direct evidence of the formation of t‐BuO^.^ by the photolysis of 1 was provided by the ESR characterization of spin‐adducts of this radical with nitrosobenzene and nitrosodurene. Evidence of the photolysis of the peroxide bond in 1 is important for the mechanism of reaction of phenolic chain‐breaking antioxidants.
📜 SIMILAR VOLUMES
A photochemical precursor to a pendant conjugated polyradical has been synthesized, poly [3,5-di-tert-butyl-4-[(2,4,6-tri-tert-butylphenyl)oxalato]phenylacetylene], 3. Irradiation of 3 at 77 K in the solid state at õ 300 nm yielded poly(3-5-ditert-butyl-2-oxyphenyl acetylene), 2, with 30-40% of the
trrf-Butyl and 2,6-di(tert-butyl)-4-methylphenyl (RHT) cyclopropanecarboxylates (4, 6, 24, 25) are lithiated with LiN(i-Pr), and t -BuLi, respectively. Reactions with alkyl halides, aldehydes, acyl chlorides, and heteroelectrophiles give a-substituted BHT esters which can be cleaved (t-BuOK/H,O/THF)