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Synlett 1998; 1998(12): 1366-1368
DOI: 10.1055/s-1998-1979
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2,3-Sigmatropic Rearrangement of Sulfonium Ylides Generated by Addition of Samarium Carbenoids

Munetaka Kunishima* , Daisuke Nakata, Chikako Goto, Kazuhito Hioki, Shohei Tani
  • *Faculty of Pharmaceutical Sciences, Kobe Gakuin University, Nishi-ku, Kobe 651-2180, Japan; Fax: +81-78-974-5689; E-mail: kunishima@pharm.kobegakuin.ac.jp
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Publication Date:
31 December 2000 (online)

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Allylic sulfides are transformed into homoallylic sulfides with complete allylic inversion by treatment with SmI2 and CH2I2 in THF. The reaction will involve allylic sulfonium ylides as an intermediate, which undergoes 2,3-rearrangement.

2,3-rearrangement - samarium iodide - sulfonium ylides - samarium carbenoids - allylic sulfides