Synthesis, structure, and properties of {(Me₃Si)₂CH}₂SnH(OH)

The Lappert stannylene SnR₂, R = CH(SiMe₃)₂, adds water and methanol to yield the low-melting-point, crystalline hydroxy- and methoxydiorganostannanes R₂SnH(OH) (1) and R₂SnH(OMe) (2). The corresponding deuterated derivatives R₂SnD(OD) (1-d₂) and R₂SnD(OCD₃) (2-d₄) have also been prepared. Compounds 1 and 2 react with D₂O with retention of the Sn−H bond to give R₂SnH(OD) (1-d(SnOD)). The reaction is thought to proceed by an SN₂ type mechanism via a [R₂SnH(OR‘)₂]- (R‘ = H, D, or Me) intermediate or transition state. Consistent with this, 2-d₄ is hydrolyzed to R₂SnD(OH) (1-d(SnD)). A single-crystal X-ray structure analysis of 1 reveals that individual molecules form Ci-symmetrical dimers in the solid with short O−H···O* hydrogen bridges (O···O* = 2.854(2) Å). Reaction of 1 with (ⁱPr₂PC₂H₄PⁱPr₂)Pd(C₂H₄) results in oxidative addition of the Sn−H bond to Pd⁰ to give the known (ⁱPr₂PC₂H₄PⁱPr₂)Pd(H)−SnR₂(OH) (3)