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

Authors
Zhang, C Ito, H Maeda, Y Shirai, N Ikeda, S Sato, Y
Citation
C. Zhang et al., Novel isomerization reaction of N,N-dimethyl-alpha- (methoxycarbonyl)-4-substituted-benzylammonium N-methylides, J ORG CHEM, 64(2), 1999, pp. 581-586
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
2
Year of publication
1999
Pages
581 - 586
Database
ISI
SICI code
0022-3263(19990122)64:2<581:NIRON(>2.0.ZU;2-X
Abstract
Fluoride ion-induced desilylation of N,N-dimethyl-N-[(trimethylsilyl)methyl ]-alpha-(methoxycarbonyl)- 4-substituted benzylammonium salts (7) gave two Stevens rearrangement products: methyl 3-(dimethylamino)-2-(4-substituted p henyl)propionates (13) from N-methylides 8, and methyl 3-(dimethylamino)-3- (4-substituted phenyl)propionates (15) from N-benzylides 10. Additional Ste vens rearrangement products, methyl 2-(dimethylamino)-3-(4-substituted phen yl)propionates (16), were competitively formed from ylides 12 when the cesi um fluoride used was not predried. The mechanism of the isomerization from methylides 8, which was initially generated, to 10 and 12 is discussed.