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  1. 学術雑誌論文

Inverse electron-demand 1,3-dipolar cycloaddition of nitrile oxide with common nitriles leading to 3-functionalized 1,2,4-oxadiazoles

http://hdl.handle.net/10173/1370
http://hdl.handle.net/10173/1370
9c7dfb51-042b-4eae-866a-ebfca87172d8
名前 / ファイル ライセンス アクション
27-18.pdf 27-18.pdf (215.3 kB)
Item type 学術雑誌論文 / Journal Article(1)
公開日 2016-03-25
タイトル
タイトル Inverse electron-demand 1,3-dipolar cycloaddition of nitrile oxide with common nitriles leading to 3-functionalized 1,2,4-oxadiazoles
言語
言語 eng
資源タイプ
資源タイプ識別子 http://purl.org/coar/resource_type/c_6501
資源タイプ journal article
著者 Nishiwaki, Nagatoshi

× Nishiwaki, Nagatoshi

WEKO 1020

Nishiwaki, Nagatoshi

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Kobiro, Kazuya

× Kobiro, Kazuya

WEKO 1021

Kobiro, Kazuya

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Hirao, Shotaro

× Hirao, Shotaro

WEKO 1022

Hirao, Shotaro

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Sawayama, Jun

× Sawayama, Jun

WEKO 1023

Sawayama, Jun

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Saigo, Kazuhiko

× Saigo, Kazuhiko

WEKO 1024

Saigo, Kazuhiko

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Ise, Yumiko

× Ise, Yumiko

WEKO 1025

Ise, Yumiko

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Okajima, Yoshikazu

× Okajima, Yoshikazu

WEKO 1026

Okajima, Yoshikazu

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Ariga, Masahiro

× Ariga, Masahiro

WEKO 1027

Ariga, Masahiro

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抄録
内容記述タイプ Abstract
内容記述 A carbamoyl-substituted nitrile oxide was generated upon treatment of easily available 2-methyl-4-nitro-3-isoxazolin-5(2H)-one with THF (not dried); the reaction proceeded efficiently even in the absence of any special reagents and reaction conditions. The nitrile oxide caused 1,3-dipolar cycloaddition with common aliphatic nitriles or electron-rich aromatic nitriles to afford 3-functionalized 1,2,4-oxadiazoles, which are expected to serve as precursors for the preparation of a variety of functional materials by the chemical transformation of the carbamoyl group. While conventional preparative methods for 1,2,4-oxadiazoles involve the cycloaddition of an electron-rich nitrile oxide with an electron-deficient nitrile or a nitrile activated by a Lewis acid, our method employs the complementary combination of an electron-rich nitrile and an electron-deficient nitrile oxide- the inverse electron-demand 1,3-cycloaddition. The DFT calculations using B3LYP 6-31G* supported the abovementioned inverse reactivity, and also suggested the presence of an accelerating effect by the carbamoyl group as a result of hydrogen bond formation with a dipolarophilic nitrile.
書誌情報 Organic & Biomolecular Chemistry

巻 9, 号 19, p. 6750-6754, 発行日 2011
DOI
関連タイプ isVersionOf
識別子タイプ DOI
関連識別子 10.1039/C1OB05682D
権利(URI)
権利情報 http://pubs.rsc.org/en/Content/ArticleLanding/2011/OB/c1ob05682d#!divAbstract | http://pubs.rsc.org/en/Content/ArticleLanding/2011/OB/c1ob05682d#!divAbstract
著者版フラグ
出版タイプ AM
出版タイプResource http://purl.org/coar/version/c_ab4af688f83e57aa
出版者
出版者 Royal Society of Chemistry
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