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- W2034377761 abstract "The photochemical reaction of ortho-quinones with triarylketenimines 4 yields quantitatively the dihydrodioxin derivatives 5 via a (4 + 2)-cycloaddition. Kinetic studies on the photochemical reaction of phenanthrenequinone (PQ) with N-(p-tolyl)dipheriylketenimine show that the reaction proceeds irreversibly, probably via an exciplex of triplet PQ with the CC double bond and an allylic biradical: k2 = (1.18 ± 0.03)·109 1·mol−1·s−1 at 25°C in benzene (Scheme 2). Competition experiments between triplet PQ and N-phenyl-substituted triphenylketenimines (Ph2C = C = N − C6H4 − X) gave a good correlation between the relative rate constants and the normal Hammett σ-constants ρ = −0.31, which indicates the absence of conjugation between the substituent X and the reaction centre at the C C double bond and confirms the electrophilic character of triplet phenantrenequinone. From the Taft's DSP equation it follows that the blending constant λ = ρI/ρR = 1.02." @default.
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- W2034377761 date "1985-01-01" @default.
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- W2034377761 title "The photochemical (4 + 2)-cycloaddition of ortho -quinones to triarylketenimines" @default.
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- W2034377761 doi "https://doi.org/10.1002/recl.19851040202" @default.
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