Synthesis of Some Substituted Furans and Endoperoxides Via Singlet Oxygen Reactions

Abstract

Cinnamaldehyde was used to condense with substituted acetophenone then with acetone to form substituted 2,4diene -1pentanone (14), after two moles of cinnamaldehyde condense with one mole of acetone to form 1, 5diphenyl nona8tetraene -5 – one (5), for these reactions, sodium hydroxide was used as a catalyst, the resulted compounds reduced by Luche (specific reduction agent use cerium chloride as a catalyst with sodium borohydride to protect double bond) reaction to form 2,4diene-1methoxy pentane (6-9) and -5methoxy nona1,3,6,8 – tetraene – 1,9 diyl dibenzene (10), the resulted dienes compound converted to endoperoxides (1115) via singlet oxygen reaction in the present of Rose Bengal as a catalyst with light in chlorinated solvent and finally by appling of Appel reaction condition these compounds converted to furans (1620). All mechanisms of the reaction were listed. These compounds were identified by thin layer chromatography TLC, and by their physical properties in addition, the IR spectroscopy and HNMR.