1026471-76-0Relevant academic research and scientific papers
5,6-Bis(trimethylsilyl)benzo[c]furan: An isolable versatile building block for linear polycyclic aromatic compounds
Chan, Siu-Hin,Yick, Chung-Yan,Wong, Henry N.C
, p. 9413 - 9422 (2002)
Benzo[c]furans are a class of interesting and highly reactive compounds that readily undergo Diels-Alder cycloaddition with dienophiles to restore their aromaticity. Initially, the s-tetrazine approach established by Warrener was chosen for the synthesis of the title molecule. However, it was discovered that the rate of production of isobenzofuran from this approach was too slow to react with the fugitive arynes. Consequently, an alternative route was employed to realize the title molecule in a neat state. In this way, the reactions between the title molecule and arynes were successfully achieved. Herein, two synthetic approaches towards the title molecule and its further manipulation for the preparation of silylated linear polycyclic aromatic hydrocarbons (PAH) were reported.
Improved and practical synthesis of [2,4,5-tris(trimethylsilyl)- Phenyl](phenyl)iodonium triflate and utilization as a 1,4-benzdiyne synthon
Gondo, Keisuke,Kitamura, Tsugio
, p. 2107 - 2112 (2014/07/07)
An efficient and improved method for preparing [2,4,5-tris(trimethylsilyl) phenyl](phenyl)iodonium triflate as a 1,4-benzdiyne synthon was developed by using phenyiodonium diacetate/boron triflouride diethyl etherate [PhI(OAc) 2/BF3 OEt2] reagent. The iodonium triflate generated 3,4-bis(trimethylsilyl)benzyne quantitatively to give cycloadducts with tetraphenylcyclopentadienone, furan and anthracene in high yields. These cycloadducts bearing two trimethylsilyl groups were transformed into the corresponding aryne precursors, which underwent subsequent cycloaddition reactions to afford polycyclic aromatic compounds such as 1,4-dihydro-1,4- epoxyanthracene, naphthotriazole, triptycene, and anthratriazole derivatives in good to high yields. The total reactions are formally considered as double cycloaddition reactions of 1,4-benzdiyne. This practical and useful formal benzdiyne strategy is described.
A mild and efficient method for the synthesis of mixed adducts of 1,4-bis-benzyne
Winling, Alain,Russell, Richard A.
, p. 3921 - 3923 (2007/10/03)
Unsymmetrical adducts of 1,4-bis-benzyne ? have been prepared by the addition of dienes to mohobenzynes generated sequentially from 1,2,4,5-tetrakis(trimethylsilyl)benzene.
