TY - JOUR
T1 - Novel isomerization reaction of N,N-dimethyl-α-(methoxycarbonyl)-4- substituted-benzylammonium N-methylides
AU - Zhang, Chen
AU - Ito, Hiroto
AU - Maeda, Yasuhiro
AU - Shirai, Naohiro
AU - Ikeda, Shin Ichi
AU - Sato, Yoshiro
PY - 1999/1/22
Y1 - 1999/1/22
N2 - 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.
AB - 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.
UR - https://www.scopus.com/pages/publications/0033593516
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U2 - 10.1021/jo981729h
DO - 10.1021/jo981729h
M3 - Article
AN - SCOPUS:0033593516
SN - 0022-3263
VL - 64
SP - 581
EP - 586
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -