Synthesis of 2-(phenoxymethyl)oxirane derivatives through unexpected rearrangement of oxiran-2-ylmethyl benzenesulfonates.

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المؤلفون: Shen, Chuang¹ (AUTHOR); Guo, Xiang¹ (AUTHOR); Yu, Jun¹ (AUTHOR); Zeng, Xian-Guo¹ (AUTHOR); Peng, Li¹ (AUTHOR); Zhao, Chuan-meng¹ (AUTHOR); Zhang, Fu-Li¹ (AUTHOR)
المصدر:
Synthetic Communications. 2017, Vol. 47 Issue 4, p273-278. 6p.
الموضوع:
*ETHYLENE oxide; *BENZENESULFONATE analysis; *ORGANIC compound analysis; *FUNCTIONAL groups; *ORGANIC chemistry

معلومة اضافية
- نبذة مختصرة :
  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. [ABSTRACT FROM AUTHOR]