Bulletin of the Chemical Society of Japan · 1971 · 18 citations · 5 references
Natural SciencesChemistryBioorthogonal ChemistryOrganic ChemistryOrganometallic ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsPhotocatalysisPhotochemical SynthesisPhotochemistryBicyclononyne ChemistryHeterocyclic ReactivityPhotochemical Reaction MechanismsPhotocyclization ReactionsRing Size Effects
Abstract The photoreactions of 11-, 12-, and 13-membered cycloalkanones (Ia, Ib, and Ic) are described. The major products are cis, trans isomers of bicyclo[n.2.0]alkan-1-ol (n=7, 8, and 9; II, III). The stereochemistry and multiplicity of the reactive species have been discussed with emphasis on the effect of the ring size. The Ib cyclododecanone is most readily susceptible to the photochemical cyclization via its S1 state, affording the cis-cyclobutanol IIb stereoselectively.
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