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Photochemistry of 4,4-Dialkoxy-2,5-cyclohexadienones

✍ Scribed by Paul Margaretha

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
250 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Irradiation (λ > 370 nm) of 4,4‐dimethoxy‐2,5‐cyclohexadienone (1 a) in benzene affords mainly the ketene acetal 4 a, which then undergoes further rearrangement. The carbomethoxycyclopentenones 6 and 7 were isolated in modest yields (10–15°). It is conceivable that the latter results from decomposition of the unobserved bicyclohexenone 5 a, the formation of which could be expected by analogy to e.g. 1 c → 5 c. Compound 4 a is presumably formed via 1,2 hydrogen shift from the intermediate zwitterion 3 a. Under similar irradiation conditions 1,4‐dioxa‐spiro[4.5] deca‐6,9‐dien‐8‐one (1 b) gave 4 b as the only definable product. In i‐C~8~H~18~ 1 a gave p‐methoxyphenol (8) as the only product, most probably via hydrogen abstraction.

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## 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 rea