The reactivity of tetramesityldisilene with epoxides: Dependence of product distributions on steric and structural characteristics of the epoxide

Article abstract of DOI:10.1016/0022-328X(95)06069-9

Mono- and 1,1-disubstituted epoxides react with tetramesityldisilene (1) to give disilyl enol ethers (5) five-membered rings (6) and the products of epoxide deoxygenation, alkenes and 1,1,2,2-tetramesityl-3-oxa-1,2-disilacyclopropane (4). Adducts 5 and 6 are formed with complete regioselectivity, suggesting involvement of an epoxide ring-opened intermediate. Product ratios vary systematically with a dependence on the steric properties of the epoxide. Single crystal X-ray diffraction results are given for 6a and 6g, the five-membered ring products derived from propylene and cyclohexene oxides.