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• W1978624646 abstract "We recently described a new photochemical rearrangement which we termed a Type C process. The reaction involves a δ to α aryl migration in 5-disubstituted cyclohexenones also having bulky C-3 substituents. In contrast to most cyclohexenone rearrangements, the reaction occurs via a twisted π−π* excited triplet rather than the usual n−π* state. The electronic nature of the rearrangement was assessed using migration selectivity with p-anisyl and p-cyanophenyl groups. A synthesis of the reactants was elaborated, and the product structures were established by X-ray and NMR analysis. The reaction mechanism was established further with DFT and CASSCF computations. In the latter, localized NBO basis orbitals permitted proper selection of the active space. The nature of the diradical intermediates as well as the transition states was established computationally. Sensitization experiments with regioselectivities the same as those in direct irradiation confirmed the triplet multiplicity of the process." @default.
• W1978624646 created "2016-06-24" @default.
• W1978624646 creator A5064299578 @default.
• W1978624646 creator A5083690067 @default.
• W1978624646 date "2003-04-11" @default.
• W1978624646 modified "2023-10-16" @default.
• W1978624646 title "An Experimental and Theoretical Study of the Type C Enone Rearrangement: Mechanistic and Exploratory Organic Photochemistry¹" @default.
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• W1978624646 doi "https://doi.org/10.1021/ja028631b" @default.
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