Reactivity of benzylic carbanions IX. [1,4] rearrangement of the Me3Si group in 9,9-bis(trimethylsilyl) 10-lithio 9,10-dihydroanthracene
作者:Michèle Daney、René Lapouyade、Brigitte Labrande、Henri Bouas-Laurent
DOI:10.1016/s0040-4039(00)71399-2
日期:1980.1
(trimethylsilyl) 10-lithio 9,10-dihydroanthracene undergoes an intramolecular [1,4] rearrangement to lead, after protonation, to cis 9,10-bis (trimethylsilyl) 9,10-dihydroanthracene (II) with a high yield. This shift, rarely encountered in anionic carbon skeletons, is believed to be favoured by structural factors and stabilisation of a carbanion α to silicon.
9,9-双(三甲基甲硅烷基)10-硫代9,10-二氢蒽经过质子化后分子内[1,4]重排导致顺式9,10-双(三甲基甲硅烷基)9,10-二氢蒽(II)高产量。据认为,这种转变是阴离子碳骨架中很少遇到的,它受结构因素和碳负离子α稳定化为硅的促进。