A New Mode for the Generation of o-Xylylene by peri-Selenium Participation from 8,13-Dihydrobenzonaphthodiselenonin under Irradiation

Article abstract of DOI:10.1021/jo00072a001

A new cyclic bis-selenide containing both benzylic methylene groups and a naphthalene ring, 8,13-dihydrobenzonaphtho<1,8-bc><1,5>diselenonin (1), was stable in the dark; however, the C-Se bond of 1 was readily cleaved to form o-xylylene (2) and naphtho<1,8-cd>-1,2-diselenole (3) under the scattered light in the laboratory.The o-xylylene generated from 1 under the scattered light or UV irradiation (254 nm) was trapped by several dienophiles.