Y. Kubo, T. Todani, Takeo Inoue
Feb 1, 1993
Citations
0
Influential Citations
6
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The photoreaction of dimethyl 1,4-naphthalenedicarboxylate (4) with allyltrimethylsilane (7) in acetonitrile–methanol gave reductive allylation products. The formation of the products is rationalized by a mechanism involving a single electron transfer from 7 to the singlet excited state of 4, an attack of the allyl radical (16) generated by a C–Si bond cleavage in the radical cation of 7 toward the radical anion of 4 to give an anionic intermediate, and protonation of the intermediate. The photoreaction of dimethyl 1,2-naphthalenedicarboxylate (2) with 7 gave reductive allylation products along with a cyclobutane, possibly by the secondary photoreaction of another reductive allylation product. The photoreactions of dimethyl 1,3-, 2,3-, and 2,6-naphthalenedicarboxylates (3, 5, and 6) with 7 gave cyclobutanes, possibly by the photoreactions of reductive allylation products. The values of the free-energy changes (ΔGet) associated with the single-electron transfer from 7 to the singlet excited states of 2—6 a...