Viewed: 17:26:25 in March 29, 2020

[Angew. Chem. Int. Ed. 2019, 58 (12), 4046−4050] The Halogen−Samarium Exchange Reaction: Synthetic Applications and Kinetics (Anthore-Dalion, Lucile; Benischke, Andreas D.; Wei, Baosheng; Berionni, Guillaume; Knochel, Paul)

Keywords: Sm; Mg; Zn; rare earth

有機亜鉛の大家、Prof. Paul Knochelらのグループによる研究です。

ⁿBu₂Sm·4LiClやⁿBuSm·5LiClによるハロゲン化アリール類のハロゲン/サマリウム交換反応についての報告のようです。ハロゲン/サマリウム交換反応により発生したアリールサマリウム種はアルデヒド、ケトン、イミン、アミド等と反応しするのですが、教科書的な有機マグネシウムの反応との差異がどんなものなのか、気になるところです。

Supporting informationにはシクロプロパン環をもつケトンとの反応例が報告されていますが、有機マグネシウムだとシクロプロパン環の開裂が起こるんだっけな、忘れた。それともラジカル反応ではないことを示したかったのか。この辺りのことは、論文本体を読まないとわからないですね。

そしてこのハロゲン/サマリウム交換反応、有機マグネシウムと臭化化アリールの臭素/マグネシウム交換よりも臭素/サマリウム交換の方が100万倍近く速いとこの論文では報告していて、その理由が炭素−金属結合のイオン性や金属の電気陰性度と関連があると要旨には記述してあります。ちなみにWikipediaによるとサマリウムとマグネシウムとリチウムの電気陰性度はそれぞれ1.17と1.31と0.98です。

個人的な興味もあり、読みたい論文に追加です。リチウムフリーの系で検討した方がいいんじゃないかなとは思いましたが、難しいか。Graphical abstractにこの反応載せるんだったら、4-tert-ブチルシクロヘキサンの反応も検討すればよかったのに。

 

Nazarov環化 (該当者なし)

米国で世界初となるテレビ放送を開始
北大西洋ポルトガル沖で地震(M8.2)
台湾全島で地震
日本海洋学会創立
日本癌学会創立
日本音楽文化協会結成
ドレミファの階名がイロハとなる
ラヂオ室(ラヂオプレス)を設置
広島無尽(もみじ銀行)設立
東海銀行設立
山陰合同銀行設立
東邦銀行設立
帝都高速度交通営団設立
名古屋鉄道新名古屋駅開業
第1回海の記念日
日本軍のマレー半島上陸および真珠湾攻撃で太平洋戦争が開戦
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ここの画像を使用しています。

那須のアルパカちゃん。

 

　

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