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査読

9 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)581-586
ページ数6
ジャーナルJournal of Organic Chemistry
64
2
DOI
出版ステータスPublished - 22-01-1999
外部発表はい

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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