Synthesis of 2-(phenoxymethyl)oxirane derivatives through unexpected rearrangement of oxiran-2-ylmethyl benzenesulfonates |
| |
| Authors: | Chuang Shen Xiang Guo Jun Yu Xian-Guo Zeng Li Peng Chuan-meng Zhao |
| |
| Institution: | China State Key Laboratory of New Drug and Pharmaceutical Process, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, Shanghai, China |
| |
| Abstract: | The synthesis of 2-(phenoxymethyl)oxirane derivatives from oxiran-2-ylmethyl benzenesulfonates was developed through a base promoted rearrangement. A new C-O bond was formed along with the unexpected cleavage of C-S bond via this process. This unusual reaction was characterized with mild reaction conditions, high efficiency, and excellent functional group tolerance. A plausible reaction mechanism was proposed on the basis of experimental results and control experiments. |
| |
| Keywords: | 2-(Phenoxymethyl)oxirane C–S cleavage oxiran-2-ylmethyl benzenesulfonate potassium hydroxide rearrangement |
|
