117203-20-0Relevant academic research and scientific papers
Stereoselectivity of Triplet Photocycloadditions:1 Diene-Carbonyl Reactions and Solvent Effects
Griesbeck, Axel G.,Buhr, Stefan,Fiege, Maren,Schmickler, Hans,Lex, Johann
, p. 3847 - 3854 (1998)
The diastereoselectivity of the photocycloaddition of benzaldehyde to furan was determined (exo/ endo = 212:1) and compared with the reaction of other carbonyl compounds and carbonyl analogues. These results were compared with Paterno-Buechi reactions of cycloalkenes and cyclic enol ethers. An increase in steric demand of the α-substituent in benzoyl compounds led to a change in exo/ endo-selectivity for furan cycloadditions that was not observed for cycloalkenes or cyclic enol ethers. Different ISC-reactive conformers with enhanced spin-orbit coupling are postulated as a reasonable explanation for the stereoselectivities observed. Additionally, solvent effects were studied, demonstrating the influence of photoinduced electron-transfer steps on the regio- and diastereoselectivity of Paterno-Buechi reactions with 2,3-dihydrofuran in polar solvents. Two bicyclic oxetanes (8 and 10) were characterized by X-ray structure analysis.
Photochemical 2 + 2 Cycloaddition of Arenecarboxylic Acid Esters to Furans and 1,3-Dienes. 2 + 2 Cycloreversion of Oxetanes to Dienol Esters and Ketones
Cantrell, Thomas S.,Allen, Andrew C.,Ziffer, Herman
, p. 140 - 145 (2007/10/02)
Methyl benzoate and other simple arenecarboxylic acid esters have been found to undergo 2 + 2 photochemical cycloaddition at the carbonyl group to furans and certain 1,3-dienes.These additions afford mixtures of oxetanes and their 2 + 2 cycloreversion products: 4-aryl-4-alkoxy-1,3-butadienyl formates and acetates (from furan oxetanes) and dienyl aldehydes and ketones (from cyclic 1,3-dienes).
