104513-01-1Relevant articles and documents
Synthesis and Properties of Amidoalkenes involving Azidoalkenoates and 1-Phenylalkan-1-ols
Lie Ken Jie, Marcel S. F.,Lam, Wilson L. K.,Lao, H. B.
, p. 1 - 11 (2007/10/02)
(Z)-Methyl 12-azido-octadec-9-enoate was converted into several amido derivatives (1a-f) when treated with short-chain alkanoic, amino, or aromatic acids in the presence of triphenylphosphine. 1-Phenylalkan-1-ols (2a-c) were prepared and converted into the 1-amino-1-phenylalkanes (3a-d) by reaction of their tricarbonylchromium complexes with acetonitrile or benzene-acetonitrile in sulphuric acid.The amide derivatives were characterized by spectroscopic and mass spectral analyses.In the 1H n.m.r. analysis the amide proton (NHCO) shift appeared at δ 5.4-5.9 and 4.9-6.03 for the C18 amidoalkenoates and 1-amido-1-phenylalkanes respectively.The amide carbonyl carbon atom (NHCO) 13C chemical shift appeared at δ 167.01-173.14 p.p.m.The mass spectral fragmentation pattern of the C18 amido fatty esters gave a characteristic base peak at m/z 114 +H2=CH-(CH2)5-CH3>, exept for (1d) where it was found at m/z 105 +CHPh>; and in the 1-amido-1-phenylalkanes the base peak appeared at m/z 106 +H2=CHPh> for (3a-c), and m/z 99 .H2Ph> for (3d).
