Structural Effects on Photochemical Cycloaddition of Phenanthrene- and Naphthalenecarboxylic Esters. Enhancement of Reactivity of an Ester Carbonyl Group by Interchromophoric Links
On irradiation in benzene, (E)-5-(p-methoxyphenyl)-4-pentenyl 3-, 9-phenanthrenecarboxylate, 1-, and 2-naphthalenecarboxylate gave novel olefinic aldehydes presumably derived from oxetane presumably derived from oxetane precursors, the intramolecular carbonyl adducts.Intermolecular carbonyl addition was not detected between the corresponding ester and olefinic chromophores.Enhancement of reactivity of the ester carbonyl group in the linked systems is discussed on the basis of experimental and theoretical studies.
Air-Driven Potassium Iodide-Mediated Oxidative Photocyclization of Stilbene Derivatives
A new method has been developed for the potassium iodide-mediated oxidative photocyclization of stilbene derivatives. Compared with conventional iodine-mediated oxidative photocyclization reactions, this new method requires shorter reaction times and affords cyclized products in yields of 45-97%. This reaction proceeds with a catalytic amount of potassium iodide and works in an air-driven manner without the addition of an external scavenger. The radical-mediated oxidative photocyclization of stilbene derivatives using TEMPO was also investigated.
1-Phenylisobenzofuran, 1-Phenylnaphthofuran, 1-Phenylnaphthofuran, and 3-Phenylnaphthofuran via Cyclic Hemiaminal, Hemiacetal, and Acetal Precursors
The title compounds have been generated via cyclic hemiaminal, hemiacetal, and acetal precursors and trapped in Diels-Alder reactions with several dienophiles.The precursors are easily prepared from o-bromobenzyl alcohol, 2-bromo-3-naphthalenemethanol, or
Smith, James G.,Fogg, Deryn E.,Munday, Ian J.,Sandborn, Richard E.,Dibble, Peter W.
p. 2942 - 2953
(2007/10/02)
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