Pyrolysis of Dibenzyl Selenides to Bibenzyls

The formation of carbon-carbon bond by sulfur extrusion such as pyrolysis of cyclic sulfones is well known as an important synthetic method, especially for the synthesis of cyclophane framework.1) Little is known about selenium extrusion as the counterpart, though organoseleniums have been properly appreciated as a useful tool for manipulating a functional group.2) Lardon reported that the thermal decomposition of dibenzyl diselenide led to a mixture of dibenzyl selenide and polyselenides.3) In contrast, recent reports showed that at 210°C, heating bis(diphenylmethyl) diselenide resulted in ready selenium extrusion to 1,1,2,2-tetraphenylethane4), and dianthrylmethyl mono- and diselenides to 1,2-dianthrylethane.5) Therefore,- it is worthwhile to study the thermal behavior of dibenzyl selenide itself.