Abstract
Generation by two different methods of silylenes stabilized by o-amino(aryl) groups is reported. The halodemetallation of difluoro or dichloro-silanes with Li metal or lithium-naphthalene gave the same product, a stabilized sila-ylide (hypercoordinated silylene). Intramolecular Lewis base stabilization is not sufficient to isolate a monomeric species. The silylenes, however, have been trapped with 2,3-dimethylbutadiene. An unexpected intramolecular rearrangement to silaacenaphthene has been observed in the case of a six-membered ring amino(aryl) coordinated silylene. Photolysis of o-1-[( N, N-dimethylamino)inethyl]-2-[tris(trimethylsilyl)silyl]benzene produced, among other products, Me 3SiSiMe 3 and the sila-ylide, which has been trapped with Et 3SiH and dimethylbutadiene. Our mechanistic interpretation is supported by spectral observation of the photochemically generated reaction intermediates in a 3-methylpentane glass at low temperature.
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