[BIS(TRIMETHYLSILYL)]SELENIDE

Chemical Properties

CLEAR COLOURLESS TO YELLOW LIQUID

Physical properties

bp 45–46°C/5.3 mmHg.

Uses

Bis(trimethylsilyl) Selenide can be used as synthesis of unsymmetrical selenides; generation of selenoaldehydes; reduction of sulfoxides, selenoxides, and telluroxides).
Bis(trimethylsilyl) selenide reacts with equimolar amounts of n-butyllithium to generate Me3SiSeLi, alkylation of which then provides trimethylsilyl alkyl selenides. Similar treatment of Me3SiSeR with BuLi / R2X successfully leads to unsymmetrical selenides in good yields (eq 5).Use of acid chlorides in place of alkyl halides results in the formation of selenoesters.

Preparation

In the initial studies, bis(trimethylsilyl) selenide was synthesized by the following two methods: silylation of sodium selenide (or lithium selenide) with chlorotrimethylsilane (eq 1) or reaction of bromobenzene, magnesium, and selenium with chlorotrimethylsilane (eq 2).