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1-亚烷基-2-氧代烯丙基阳离子与呋喃的区域选择性反应:[4 + 3]环加成、[3 + 2]环加成及亲电取代反应的控制

Regioselective reactions of 1-alkylidene-2-oxyallyl cations with furan: control of [4 + 3] cycloaddition, [3 + 2] cycloaddition, and electrophilic substitution.

作者信息

Fujita Morifumi, Oshima Makoto, Okuno Sakuro, Sugimura Takashi, Okuyama Tadashi

机构信息

Graduate School of Material Science, Himeji Institute of Technology, University of Hyogo, Kohto, Kamigori, Hyogo 678-1297, Japan.

出版信息

Org Lett. 2006 Aug 31;8(18):4113-6. doi: 10.1021/ol061655t.

DOI:10.1021/ol061655t
PMID:16928087
Abstract

The ring opening of alkylidenecyclopropanone acetal under acidic conditions produces the 1-alkylidene-2-oxyallyl cation as an intermediate, which reacts with furan to give the [3 + 2] and [4 + 3] cycloadducts as well as an electrophilic substitution product. The product distribution is controlled by the oxy substituents of the cation and by the solvent employed.

摘要

亚烷基环丙烷酮缩醛在酸性条件下开环会生成1-亚烷基-2-氧代烯丙基阳离子中间体,该中间体与呋喃反应生成[3 + 2]和[4 + 3]环加成产物以及一种亲电取代产物。产物分布受阳离子的氧取代基和所用溶剂的控制。

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Regioselective reactions of 1-alkylidene-2-oxyallyl cations with furan: control of [4 + 3] cycloaddition, [3 + 2] cycloaddition, and electrophilic substitution.1-亚烷基-2-氧代烯丙基阳离子与呋喃的区域选择性反应:[4 + 3]环加成、[3 + 2]环加成及亲电取代反应的控制
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引用本文的文献

1
(3+2)-Cycloaddition Reactions of Oxyallyl Cations.氧代烯丙基阳离子的(3 + 2)环加成反应
Synthesis (Stuttg). 2015 Jan;47(1):22-33. doi: 10.1055/s-0034-1378918.