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

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)581-586
Number of pages6
JournalJournal of Organic Chemistry
Volume64
Issue number2
DOIs
Publication statusPublished - 22-01-1999
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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