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- W2034167576 abstract "The photochemistry of 1-acyl-2-cyclopentenes varies with the nature of the acyl group. On direct irradiation the aldehyde eliminates carbon monoxide in the singlet excited state, and the aroyl compounds cleave to allyl-aroyl radical pairs both from the singlet and triplet states. In competition to α-cleavage the methyl ketones isomerize in an allylic 1,3-acetyl shift. The lowest-lying reactive triplet of these methyl ketones, characterized as a 3(π, π*) state in the case of the 3-phenyl homologue, undergo oxadi-π-methane rearrangement to a mixture of endo- and exo-5-acetylbicyclo[2.1.0]pentanes. The ground state-acetylbicyclopentanes react in two ways at elevated temperatures: endo-exo stereomutation by selective cleavage of the central cyclopropane bond and reclosure of the 1,3-cyclopentane diradical intermediate, and a rearrangement of the endo isomer to 1-acetyl-2-cyclopentenes on a separate potential energy surface involving a formal 1,2-acetyl shift. The unusually large negative entropy of activation for this latter reaction is suggestive of a concerted electrocyclic process in which the electrons of the internal cyclopropane and the C(5)-acetyl bonds participate." @default.
- W2034167576 created "2016-06-24" @default.
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- W2034167576 date "1976-01-01" @default.
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- W2034167576 title "1-acyl-2-cyclopentenes and 5-acylbicyclo[2.1.0]pentanes: photochemical and thermal isomerizations" @default.
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- W2034167576 doi "https://doi.org/10.1016/s0040-4020(01)93785-8" @default.
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