2.

[1,2]-Wittig Rearrangement of THP Acetal Compounds: Facile Synthesis of Aromatic Tertiary Alcohols

Feng-Lei Gu, Lu-Xin Liu, Guo-Qiao Lai, Jian-Xiong Jiang, Chun-Qi Sheng, Hua-Yu Qiu and Li-Wen Xu

Org. Commun. (2011), 4:1 ; 9-17

Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, P. R. China

Abstract:Several sec-aromatic THP acetal compounds have been found to be suitable substrates for the [1,2]-Wittig rearrangement in the absence of an external electrophile, which resulted in the generation of new carbon-carbon bond and the facile synthesis of aromatic tertiary alcohols. More interestingly, an unexpected effect of chlorotrimethylsilane on this [1,2]-Wittig rearrangement of sec-aromatic THP acetal compounds was found, in which two different products involving oxidative procedure were obtained due to the competitive [1,4]-Sigmatropic rearrangement versus [1,2]-Wittig rearrangement

Keywords: Wittig rearrangement; acetal compound; alcohol; radical reaction; organosilicon