Novel isomerization reaction of N,N-dimethyl-α-(methoxycarbonyl)-4- substituted-benzylammonium N-methylides

Chen Zhang, Hiroto Ito, Yasuhiro Maeda, Naohiro Shirai, Shin Ichi Ikeda, Yoshiro Sato

研究成果: Article

9 引用 (Scopus)

抜粋

Fluoride ion-induced desilylation of N,N-dimethyl-N- [(trimethylsilyl)methyl]-α-(methoxycarbonyl)4-substituted benzylammonium salts (7) gave two Stevens rearrangement products: methyl 3-(dimethylamino)- 2-(4-substituted phenyl)propionates (13) from N-methylides 8, and methyl 3- (dimethylamino)-3-(4-substituted phenyl)propionates (15) from N-benzylides 10. Additional Stevens rearrangement products, methyl 2-(dimethylamino)-3- (4-substituted phenyl)propionates (16), were competitively formed from ylides 12 when the cesium fluoride used was not predried. The mechanism of the isomerization from methylides 8, which was initially generated, to 10 and 12 is discussed.

元の言語English
ページ(範囲)581-586
ページ数6
ジャーナルJournal of Organic Chemistry
64
発行部数2
DOI
出版物ステータスPublished - 22-01-1999
外部発表Yes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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