Ortho-[2,3]-wittig rearrangement of benzyl propargyl ethers: Striking preference over the competing [1,2]-wittig shift

Katsuhiko Tomooka; Manabu Harada; Takayuki Hanji; Takeshi Nakai

doi:10.1246/cl.2000.1394

Ortho-[2,3]-wittig rearrangement of benzyl propargyl ethers: Striking preference over the competing [1,2]-wittig shift

Katsuhiko Tomooka, Manabu Harada, Takayuki Hanji, Takeshi Nakai

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

Treatment of benzyl γ-(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.

Original language	English
Pages (from-to)	1394-1395
Number of pages	2
Journal	Chemistry Letters
Issue number	12
DOIs	https://doi.org/10.1246/cl.2000.1394
Publication status	Published - 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1246/cl.2000.1394

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abstract = "Treatment of benzyl γ-(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.",

author = "Katsuhiko Tomooka and Manabu Harada and Takayuki Hanji and Takeshi Nakai",

year = "2000",

doi = "10.1246/cl.2000.1394",

language = "English",

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journal = "Chemistry Letters",

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publisher = "The Chemical Society of Japan",

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T2 - Striking preference over the competing [1,2]-wittig shift

AU - Tomooka, Katsuhiko

AU - Harada, Manabu

AU - Hanji, Takayuki

AU - Nakai, Takeshi

PY - 2000

Y1 - 2000

N2 - Treatment of benzyl γ-(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.

AB - Treatment of benzyl γ-(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.

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Ortho-[2,3]-wittig rearrangement of benzyl propargyl ethers: Striking preference over the competing [1,2]-wittig shift

Abstract

All Science Journal Classification (ASJC) codes

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