Ring-opening reactions of cyclic ethers with diiodo- and dibromodimethylsilane equivalents

  • Ohshita J
  • Izumi Y
  • Lu Z
 et al. 
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Abstract

Ring-opening halosilation of cyclic ethers with reagents of (Me2N)2SiMe2/4MeI (1a) and (Me2N)2SiMe2/4allylBr (1b) was studied. Tetrahydrofuran and cyclohexene oxide reacted with 1a and 1b to give ring-opened di(haloalkoxy)dimethylsilanes in good yield. With less strained tetrahydropyran, however, only reagent 1a gave the ring-opened product. Reactions of reagents 1a and 1b with propylene oxide also proceeded smoothly, although the regioselectivity was rather low. When similar reactions were carried out with (Me2N)2SiMe2/2MeI (2a) and (Me2N)2SiMe2/2allylBr (2b) in a ratio of cyclic ethers/2a or 2b = 1/1, the corresponding 1:1 adducts were obtained. © 2006 Elsevier B.V. All rights reserved.

Author-supplied keywords

  • Bromosilane
  • Cyclic ether
  • Halosilation
  • Iodosilane

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Authors

  • Joji Ohshita

  • Yuki Izumi

  • Zhou Lu

  • Junnai Ikadai

  • Atsutaka Kunai

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