Chemistry Letters, Vol.29, No.12, 1394-1395, 2000
Ortho-[2,3]-Wittig rearrangement of benzyl propargyl ethers: Striking preference over the competing [1,2]-Wittig shift
Treatment of benzyl gamma-(trimethylsilyl)propargyl ether with n-BuLi is shown to afford the rarely precedent ortho-[2,3]-Wittig product in remarkable preference to the [1,2]-Wittig product. The factors governing the periselectivity in this type of carbanion rearrangement are discussed.