Citation: Wu Xiang, Li Wei-Dong Z.. Unexpected Grob-type fragmentation of vinylogous β-silyloxy-cyclobutanone into γ-lactone[J]. Chinese Chemical Letters, ;2017, 28(5): 968-970. doi: 10.1016/j.cclet.2016.12.017 shu

Unexpected Grob-type fragmentation of vinylogous β-silyloxy-cyclobutanone into γ-lactone

Wu Xiang ^a ,
Li Wei-Dong Z. ^b,,

a.
School of Chemistry and Chemical Engineering, Hefei University of Technology, Hefei 230009, China
b.
Innovative Drug Research Centre, Chongqing University, Chongqing 401331, China

Corresponding author: Li Wei-Dong Z., wuxiang@hfut.edu.cn; wdli@cqu.edu.cn
Received Date: 26 October 2016
Revised Date: 24 November 2016
Accepted Date: 2 December 2016
Available Online: 16 May 2016

Figures(5)

An unusual formal oxy transposition of vinylogous β-silyloxy-cyclobutanone 1 (a 1, 5-difunctionalized substrate) under mild acidic conditions (aqueous HF in CH₃CN at 0℃) to the decalinic γ-lactone 2 was described. A plausible mechanistic pathway involving the Grob-type fragmentation and intramolecular γ-lactonization was proposed.
- Grob fragmentation,
- Vinylogous β-silyloxy-cyclobutanone,
- Decalinic γ-lactone,
- Oxy transposition,
- Intramolecular γ-lactonization
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