alpha- and beta- (N-arylamino)propanoic acid;
thermal gas-phase elimination;
theoretical analysis;
D O I:
10.1016/j.tet.2004.01.087
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
2-(N-Phenylamino)propanoic acid la and 3-(N-phenylamino)-propanoic acid 2a together with four of their aryl analogues were pyrolysed in the gas-phase. The reactions were homogeneous and free from catalytic and radical pathways. Analysis of the pyrolysate of 1 showed the elimination products to be carbon monoxide, acetaldehyde and aniline, while the pyrolysate of 2 reveals the formation of acrylic acid in addition to aniline. Theoretical study of the pyrolysis of 2 using an ab initio SCF method lend support to a reaction pathway involving a 4-membered cyclic transition state. (C) 2004 Elsevier Ltd. All rights reserved.