134271-35-5Relevant articles and documents
Synthesis of 9,10-dihydrosilaanthracenes with substituents ortho to the silicon and methylene bridges
Bedard, Thomas C.,Corey, Joyce Y.,Lange, Lura D.,Rath, Nigam P.
, p. 261 - 272 (2007/10/02)
The generation of 9,10-dihydrosilaanthracenes with substituents on benzo ring carbons, specifically in the 4,5-positions adjacent to the methylene bridge, has been developed.Attempts to prepare the 1,8-isomer where the substituents are adjacent to the silicon bridge are also described.The diarylmethane precursors to the substituted 9,10-dihydrosilaanthracenes required the synthesis of 2,3-dihalotoluenes as well as isomeric 2,6-disubstituted benzaldehydes which were then condensed to diarylmethanols through the Grignard reagents.Ring closure to the 4,5-dimethyl-9,9-dialkyl-9,10-dihydro-9-silaanthracene, I, required the use of Rieke magnesium.The structure of I (alkyl = iPr) was determined and demonstrates that the introduction of substituents adjacent to the methylene bridge causes the dihydrosilaanthracene framework to become nearly planar with a dihedral (or butterfly) angle of 170 deg C.