<b>Organosilicon chemistry I: cyclopropanation by carbene or carbenoid addition to an allylic silane</b>

• Main Authors: E.O. Dare, Ling-Kang Liu
• Format: Article
• Language: English
• Published: Chemical Society of Ethiopia 2006-06-01
• Series: Bulletin of the Chemical Society of Ethiopia
• Subjects: Cyclopropanation; Phase transfer catalyst; Dichlorocarbene; Zn-Cu couple; Simmons-Smith reaction
• Online Access: http://www.ajol.info/index.php/bcse/article/view/21143
• ISSN: 1011-3924; 1726-801X

The syntheses of tetra(dichlorocyclopropane)silane <b>2</b> and tetra(cyclo- propane)silane <b>3</b> have been accomplished using dichlorocarbene (:CCl2) and carbenoid addition, respectively. Various phase transfer catalysts (PTC) have been tested for :CCl2 addition to tetraallylsilane <b>1</b>. 2-Benzilidine-N,N,N,N',N',N',-hexaethyl propane-1,3-diammonium dibromide (Dq-Br) was found to be effective in giving <b>2</b> in a yield above 80%. A modified synthetic route to <b>3</b> by the reaction of <b>1</b> with Zn-Ag couple and methylene iodide is also described. The success of the reaction has been attributed to an alternative work-up procedure.