TY - JOUR

T1 - Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines

AU - Konev, A.S.

AU - Novikov, M.S.

AU - Khlebnikov, A.F.

PY - 2007/2

Y1 - 2007/2

N2 - N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-pi-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dirnethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-pi-cyclization, in the presence of acid catalysts suffer isomerization into alpha-fluoroimines and 1,3-disubstituted indoles.

AB - N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-pi-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dirnethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-pi-cyclization, in the presence of acid catalysts suffer isomerization into alpha-fluoroimines and 1,3-disubstituted indoles.

KW - 1,3-DIPOLAR CYCLOADDITION

KW - GENERATION

KW - DIFLUOROCARBENE

KW - PYRROLIDINES

KW - DERIVATIVES

KW - OLEFINS

KW - EXAMPLE

KW - ROUTE

U2 - 10.1134/S1070428007020224

DO - 10.1134/S1070428007020224

M3 - статья

VL - 43

SP - 286

EP - 296

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 2

ER -