Photochemically generated trimethylsilylphenylsilylene reacted with octyl chloride and cyclopropylcarbinyl chloride to give the respective formal carbon-chlorine insertion products. With sec-butyl chloride, trimethylsilylphenylsilylene afforded both the carbon-chlorine insertion product and 1-chloro-1phenyl-2,2,2-trimethyldisilane (IV), while with tert-butyl chloride, IV was obtained as the sole volatile