Organoaluminium assisted rearrangements of five-membered ring enol ethers with vinyl substituents

Ichiro Mori; Kazuhiko Takai; Koichiro Oshima; Hitosi Nozaki

doi:10.1016/0040-4020(84)85080-2

Organoaluminium assisted rearrangements of five-membered ring enol ethers with vinyl substituents

Ichiro Mori, Kazuhiko Takai, Koichiro Oshima, Hitosi Nozaki

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

20 Citations (Scopus)

Abstract

Such organoaluminium reagents as ⁱBu₃A1, PhC=CA1Et₂, and Et₂A1SPh mediate the title reactions in three different directions. (1) [3,3]sigmatropic rearrangement producing 7-membered rings. (2) isomerization to form vinylcyclopropane derivatives and (3) S_N2 type reaction with phenylthio anion via oxolane ring opening.

Original language	English
Pages (from-to)	4013-4018
Number of pages	6
Journal	Tetrahedron
Volume	40
Issue number	20
DOIs	https://doi.org/10.1016/0040-4020(84)85080-2
Publication status	Published - 1984
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Organoaluminium assisted rearrangements of five-membered ring enol ethers with vinyl substituents",

abstract = "Such organoaluminium reagents as iBu3A1, PhC=CA1Et2, and Et2A1SPh mediate the title reactions in three different directions. (1) [3,3]sigmatropic rearrangement producing 7-membered rings. (2) isomerization to form vinylcyclopropane derivatives and (3) SN2 type reaction with phenylthio anion via oxolane ring opening.",

author = "Ichiro Mori and Kazuhiko Takai and Koichiro Oshima and Hitosi Nozaki",

year = "1984",

doi = "10.1016/0040-4020(84)85080-2",

language = "English",

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pages = "4013--4018",

journal = "Tetrahedron",

issn = "0040-4020",

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T1 - Organoaluminium assisted rearrangements of five-membered ring enol ethers with vinyl substituents

AU - Mori, Ichiro

AU - Takai, Kazuhiko

AU - Oshima, Koichiro

AU - Nozaki, Hitosi

PY - 1984

Y1 - 1984

N2 - Such organoaluminium reagents as iBu3A1, PhC=CA1Et2, and Et2A1SPh mediate the title reactions in three different directions. (1) [3,3]sigmatropic rearrangement producing 7-membered rings. (2) isomerization to form vinylcyclopropane derivatives and (3) SN2 type reaction with phenylthio anion via oxolane ring opening.

AB - Such organoaluminium reagents as iBu3A1, PhC=CA1Et2, and Et2A1SPh mediate the title reactions in three different directions. (1) [3,3]sigmatropic rearrangement producing 7-membered rings. (2) isomerization to form vinylcyclopropane derivatives and (3) SN2 type reaction with phenylthio anion via oxolane ring opening.

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U2 - 10.1016/0040-4020(84)85080-2

DO - 10.1016/0040-4020(84)85080-2

M3 - Article

AN - SCOPUS:0011583192

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JO - Tetrahedron

JF - Tetrahedron

IS - 20

ER -

Organoaluminium assisted rearrangements of five-membered ring enol ethers with vinyl substituents

Abstract

ASJC Scopus subject areas

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