Insertion of an Isolable Dialkylstannylene into C–Cl Bonds of Acyl Chlorides Giving Acyl(chloro)stannanes

The reactions of isolable dialkylstannylene 1 with 1-adamantanoyl, 2,2-dimethylpropanoyl, benzoyl, and substituted benzoyl chlorides afford the corresponding acyl(chloro)stannanes in good yields. Similar reactions with more reactive acetyl and propanoyl chlorides do not give the corresponding insertion products but the corresponding dichlorostannane by the overreaction. The benzoyl(chloro)stannane reacts with acetyl chloride to afford the corresponding 1,2-dione and the dichlorostannane quantitatively. Acyl(chloro)stannanes obtained were fully characterized by multinuclear NMR spectroscopy, high-resolution mass spectrometry, and by single-crystal X-ray diffraction studies.