Nitration of Quinoline 1-Oxide: Mechanism of Regioselectivity.

YOKOYAMA Akihiro, OHWADA Tomohiko, SAITO Shinichi, SHUDO Koichi

doi:10.1248/cpb.45.279

書誌事項

タイトル別名

Nitration of Quinoline 1 Oxide Mechanis

公開日: 1997

DOI

10.1248/cpb.45.279

公開者: 公益社団法人日本薬学会

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説明

The acidity dependence of orientation in the nitration of quinoline 1-oxide was investigated by using the trifluoromethanesulfonic acid (TFSA)-trifluoroacetic acid (TFA) system and the antimony pentafluoride (SbF₅)-TFSA system. These systems provide a wider range of acidity than that of aqueous sulfuric acid. Comparison of the behavior of quinoline 1-oxide and 1-methoxyquinolinium triflate in acidic and neutral media demonstrated that O-protonated quinoline 1-oxide is nitrated at the 5- and 8-positions, and the free (unprotonated) molecule is nitrated at the 4-position. This result is consistent with theoretical expectation. It was also discovered that nitration at the 5-position increasingly predominates over that at the 8-position as the acidity is increased.

収録刊行物

ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 45 (2), 279-283, 1997

公益社団法人日本薬学会

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詳細情報詳細情報について

CRID: 1390282679135870720

NII論文ID: 130003773694; 110003616470

NII書誌ID: AA00602100

DOI: 10.1248/cpb.45.279

ISSN: 13475223; 00092363

NDL書誌ID: 4163499

Web Site: http://id.ndl.go.jp/bib/4163499; https://ndlsearch.ndl.go.jp/books/R000000004-I4163499; http://www.jstage.jst.go.jp/article/cpb1958/45/2/45_2_279/_pdf

本文言語コード: en

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