Abstract
AbstractStarting from dichloro(divinyl)silane, the dialkynyl(divinyl)silanes (CH2=CH)2Si(C≡CR)2 (R = tBu, p‐tolyl, 3‐thienyl, CH2NMe2) were prepared. These silanes were treated with 9‐borabicyclo[3.3.1]nonane (9‐BBN) for 1,2‐hydroboration of the vinyl groups. The hydroboration products rearranged quickly and quantitatively by intramolecular 1,1‐carboboration into the respective target compounds, the axially chiral 5‐silaspiro[4.4]nona‐1,6‐dienes bearing boryl groups at the 2‐ and 7‐positions and the R substituents at the 1‐ and 6‐positions. Simple protodeborylation with acetic acid proved possible, except for R = tBu. The remaining Si–C function in (CH2=CH)2Si(Cl)C≡CtBu opens the way to new spirosilanes after a sequence of hydroboration/carboboration/hydroboration, for which a first example was studied. The products were characterized by X‐ray diffraction in the solid state and NMR spectroscopy in solution (1H, 11B, 13C, 15N, 29Si), complemented by optimization of gas‐phase structures and calculation of NMR parameters by DFT methods.
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