158956-25-3Relevant academic research and scientific papers
Regio-Controlled Ene-Yne Photochemical Cycloaddition Using Silicon As A Tether
Bradford, Cara L.,Fleming, Steven A.,Ward, Susan C.
, p. 4189 - 4192 (1995)
Substituted cyclobutenes were synthesized by irradiation of silicon tethered ene-ynes.Irradiation of a silicon tethered bisphenylalkyne resulted in cycloaddition and rearrangement to a substituted naphthalene.A diradical intermediate which resembles known DNA cleaving molecules is proposed. - Key Words: 2+2 photocycloaddition, alkoxysilane photochemistry, cyclobutene synthesis
Mechanistic analysis of the photocycloaddition of silyl-tethered alkenes
Fleming, Steven A.,Parent, Alexander A.,Parent, Ephraim E.,Pincock, James A.,Renault, Lise
, p. 9464 - 9470 (2008/03/14)
(Chemical Equation Presented) The photochemistry of substituted cinnamyloxy silanes has been examined in both cyclohexane and acetonitrile solvents. Alkene isomerization occurs in addition to cycloaddition. Fluorescence quantum yields and excited singlet state lifetimes have been determined for each compound. We have used the information in order to better understand the regio- and stereoselectivity of photocycloaddition between silyl-tethered cinnamyl groups. This study allows us to conclude that the 2 + 2 photocycloaddition between alkenes is not a Woodward-Hoffmann orbital symmetry controlled event. The most consistent explanation for the excellent regio- and stereoselectivity is that the photocycloaddition is conformationally controlled.
