Generation of Synthetic Equivalents of Benzdiynes from Benzobisoxadisiloles

Linear and angular benzobisoxadisiloles 14 and 16 can serve as the precursors for stepwise
generations of the syntetic equivalents of 1,4- and 1,3-benzdiynes. Benzynes generated were trapped
as [4+2] cycloaddition products. Two identical or different rings can be fused to the benzdiyne
equivalents. Highly substituted arenes were obtained by removing the oxygen bridges from the
furan adducts. The synthesis of naphthoxadisilole 28, which can serve as the precursor of 2,3-naphthyne, is also described.