[読みたい論文] そこらへんの水を食ってアルケンからオキサジアゾールノンを合成します

Viewed: 14:02:02 in December 16, 2019

Posted: July 16, 2019

tert-Butyl Nitrite Mediated Synthesis of 1,2,4-Oxadiazol-5(4H)-ones from Terminal Aryl Alkenes (Sau, Prasenjit; Rakshit, Amitava; Alam, Tipu; Srivastava, Hemant Kumar; Patel, Bhisma K.)
Org. Lett. 2019, 21 (13), 4966−4970.

Keywords: styrene; tert-butyl nitrite; DMSO


アルケンと亜硝酸tert-ブチルとH2Oから1,2,4-オキサジアゾール-5(4H)-オン化合物を合成する反応について報告しているようです。Graphical Abstractに記載の通り、化合武名の「オン」の酸素原子は水分子由来。三成分連結反応と言えなくもないですが、亜硝酸tert-ブチルのアレやコレやをロスしていますし…。

要旨を眺めてやはり気になるのが反応機構。アルケンの炭素−炭素二重結合が切断される経路、アルケンのオゾン酸化と似ているのかなと思ったりはしたのですが、Graphical Abstract上ではアルケン1分子と亜硝酸tert-ブチル2分子が反応している点(実際には3分子?)、そして、亜硝酸tert-ブチルのtert-ブチル基どころか酸素原子までをロスしている点から、論文本文を読んで反応機構をどうしても確認したくなります。そんなわけで読みたい論文に追加です。ビラジカル中間体とは?

「触媒いらんかったわ」な記述が、Supporting Informationにあります。

この記事を書いた人
「牧岡ふうふ堂」オーナー。博士(工学)。
酒都圏在住。
某地方の国立系工業大学でアシスタントをしていました。 専門は有機反応・金属錯体(主に希土類)・π共役系。
twitterアカウントは@makiokafufudo(お仕事用)、@ymakioka(個人用)です。

 

1942年はこんな年

人名反応など
Wittig転位
ノーベル化学賞
(該当者なし)

できごと
興亜工業大学(現千葉工業大学)開校
帝国石油設立
鉄道技術研究所設立
西日本鉄道(西鉄)設立
広島電鉄設立。
三井船舶(商船三井)設立
関門鉄道トンネル開業
大日本映画(大映)設立
産業経済新聞(産経新聞)創刊
西日本新聞発刊
静岡新聞創刊
東京新聞創刊
東京に初の空襲警報発令
井の頭自然文化園開園
共栄火災海上保険設立

 

きょうのどうぶつ

ここの画像を使用しています。

7月10日のお猿さん。広島市内の国道2号線から。

 

計算終わりました

 

あわせてどうぞ

SOHOのすすめ記事一覧 2019年
お仕事関係の記事のリストです(2019年)。

読みたい論文シリーズ− 2019年3Q
読みたいけと読んでいない論文を、構造式を描きながら紹介します(2019年7〜9月)。

 

[読みたい論文] π共役系の発光特性: クロロホルムの怪
CCl3と関係がありそうな。
Chem. Commun. 2019, 55 (57), 8242−8245.

[読みたい論文] 光学活性アミンの絶対配置と光学純度をシッフ塩基にして決めます
でっかいアルデヒドと反応させます。
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[読みたい論文] ピロ亜硫酸カリウムを二酸化硫黄源にしてスルホンを合成します。
ハロゲン化アリールと、Pd触媒下で。
Chem. Lett. 2019, 48 (8), 760−763.

[読みたい論文] Diels−Alder反応: ホウ素原子一つでexo選択的に?
教科書的にはendo選択的なはずがどうしてこうなった
Org. Lett. 2019, 21 (13), 5068−5072.

[読みたい論文] ほぼ環状構造の超原子価ヨウ素化合物
3価化合物の合成。
Chem. Commun. 2019, 55 (55), 7998−8000.

[読みたい論文] 添加剤不要!パラジウム触媒下でのビアリール合成
配位子なしで勝負して欲しかった。
Org. Lett. 2019, 21 (12), 4734−4738.

[読みたい論文] 臭くないチオフェオール源をチオ尿素から作ります
昔チオフェノールの生で怒られたことあります。
Chem. Eur. J. 2019, 84 (37), 8903−8910.

描くのが大変なくらいでっかい環状ラクトンを作ります。
1箇所二重結合を入れとくのがいいのでしょうか。
J. Org. Chem. 2019, 84 (12), 8019−8026.

[読みたい論文] 金属触媒を使うことなく実質ヒドロホルミル化します
環状アセタールの水素をぶっこぬきます
Chem. Lett. 2019, 48 (7), 715−717.

金属触媒を使うことなくアルデヒドを脱カルボニル化させます
アタマと反応剤は使いよう
Chem. Eur. J. 2019, 25 (36), 8508−8512.

 

注目のWebコンテンツ

 

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