Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 9, Issue 19, Pages 4732-4738Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200304961
Keywords
alkynes; organoboration; NMR spectroscopy; silanes; X-ray diffraction
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1-Boraadamantane 1 was treated with alkyn-1-ylsilanes 2 containing one or two Si-H functions. Under mild conditions, the reaction gave 4-methylene-3-borahomoadamantane derivatives 4 quantitatively and selectively by 1,1-organoboration. An electron deficient Si-H-B bridge was present in the product. ne analogous reaction of 1 with an alkyn-1-yl-disilane 3 gave the corresponding alkene derivative 5, however, without the Si-H-B bridge. Evidence for the Si-H-B bridge in 4 was given by IR data, an extensive set of NMR spectroscopical data (H-1, B-11, C-13, Si-29 NMR) including various unusual isotope effects on chemical shifts and coupling constants, as well as from the molecular structure of one example, 4e, in the solid state. The precursor of 4e, alkyne 2e, Ph2Si(H)Cequivalent toCSi(H)Ph-2, was also studied by X-ray analysis.
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