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2004
Nitriles
Q 0520
47- 084
Nitrile Anion Cyclization with Epoxysilanes Followed by Brook Rearrangement/
Ring Opening of Cyclopropane Nitriles/Alkylation. — The reaction of (I) and (V)
with a base and alkylating agents affords δ-siloxy-γ,δ-unsaturated pentanenitrile derivatives via nitrile anion cyclization with epoxysilanes, Brook rearrangement mediated
eliminative ring fissions of cyclopropanes, and α-alkylation of nitrile in a tandem fashion. Reaction of (I) with (IIIc) gives (IIa) as a product of protonation instead of the expected (IVc). — (OKUGAWA, S.; TAKEDA*, K.; Org. Lett. 6 (2004) 17, 2973-2975;
Dep. Synth. Org. Chem., Grad. Sch. Med. Sci., Hiroshima Univ., Minami,
Hiroshima 734, Japan; Eng.) — Steudel
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