[読みたい論文] スルホニルイミドでシクロプロパン化します。

Viewed: 03:34:36 in December 11, 2019

Posted: April 12, 2019

Mild and Diazo-Free Synthesis of Trifluoromethyl-Cyclopropanes Using Sulfonium Ylides (Cyr, Patrick; Flynn-Robitaille, Joël; Boissarie, Patrick; Marinier, Anne)
Org. Lett. 2019, 21 (7), 2265−2268.

Keywords: NaHMDS


カルベンやカルベノイドを使わない、アリールアルケンのシクロプロパン化について報告しているようです。トリフルオロメチル化合物限定なのかどうかはわかりませんが、温和な条件で進行する模様。炭素源はメチルスルホニウム塩。NaHMDSでスルホニウムイリドにして、アルケンと反応させていきます。

ところで、この論文での反応、スルホニウムイリドはアルケンに対してどのように反応していくのでしょうか、論文を読まずに想像しますが、多分2段階で、1段階目はスルホニウムイリドの炭素の置換基の少ない側のアルケンの炭素への求核的な反応、その次の2段階目が、アリール基が結合したアルケンの炭素のスルホニウムイリドの炭素への求核的な反応なんだろうな、と。1段目の求核的な反応がどの炭素に対して起こるのか少し悩みました。アニオンの安定性とか、共役の関与とか、分極とか。


実際のところどうなのか知りたいので、読みたい論文に追加です。

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。

 

1962年はこんな年

人名反応など
Ugi反応 [Doi 1]
Corey−Chaykovsky反応 [Doi 1]
DeMayo反応 [Doi 1]
ノーベル化学賞
球状タンパク質の構造研究
(Max Ferdinand Perutz, John Cowdery Kendrew)
できごと
Inorg. Chem.創刊
東京都が世界初の1000万都市に
日本初の家庭用柔軟仕上げ剤「花王ソフター(後のハミング)」発売(花王石鹸=花王)
西ヨーロッパ12か国共同で欧州宇宙機関創設
「キャロル360」発売(東洋工業=マツダ)
「リポビタンD」発売(大正製薬)
イエローハット設立
「フロンテ」発売(鈴木自動車工業=スズキ)
ドジャー・スタジアム?落し
「てなもんや三度笠」放送開始
「スープ付き明星ラーメン」発売(明星食品)
ジャニーズ事務所創業
コメリ設立
日本警備保障(セコム)設立
明治アーモンドチョコ発売
アメリカとイギリス・フランス間で初の大陸間衛星中継が成功
戦後初の国産旅客機YS-11完成
「花王ブリーチ(後のハイター)」発売(花王石鹸=花王)
「週刊TVガイド」創刊(東京ニュース通信社)
三宅島で火山噴火によるM5.9クラスの地震発生
ビデオリサーチ設立
若戸大橋開通
「ミニカ」発売(新三菱重工業)
ビートルズレコードデビュー
NHK杯テレビ囲碁トーナメントが番組開始
キューバ危機
「キユーピー3分クッキング」放送開始
ボブ・ディランレコードデビュー
首都高速道路最初の供用区間開通(京橋〜芝浦)
日本でリニアモーターカーの研究が始まる

 

きょうのどうぶつ

ここの画像を使用しています。

散歩中に見かけたわんこ。毛並みはいいが、野良っぽい。

 

きょうの計算

 

あわせてどうぞ

SOHOのすすめ記事一覧 2019年
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ナノ粒子 パラジウム  
[J. Mater. Chem. A 20190411021512, 2019, 15−8855]
Interface engineering of palladium and zinc oxide nanorods with strong metal–support interactions for enhanced hydrogen production from base-free formaldehyde solution
(Du, Leilei; Qian, Kaicheng; Zhu, Xiaohui; Yan, Xiaoqing; Kobayashi, Hisayoshi; Liu, Zhiqi; Lou, Yupeng; Li, Renhong)
Tag: ZnO, Zn, Pd, Cat, ET, H, FA, HCHO, Ea, NP, e-, C

リチウムイオン二次電池  
[J. Mater. Chem. A 20190411021559, 2019, 15−8845]
Oxygen loss and surface degradation during electrochemical cycling of lithium-ion battery cathode material LiMn2O4
(Gao, Xiang; Ikuhara, Yumi H.; Fisher, Craig A. J.; Huang, Rong; Kuwabara, Akihide; Moriwake, Hiroki; Kohama, Keiichi; Ikuhara, Yuichi)
Tag: EC, CT, Li, O, EM, STEM, LIB, TEM, e-, TF