Synthesis and properties of amidoalkenes involving azidoalkenoates and 1-phenylalkan-1-ols

Abstract

(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-amido-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 amido alkenoates 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 [[graphic omitted]H₂CH(CH₂)₅CH₃], except for (1d) where it was found at m/z 105 [[graphic omitted]CPh]; and in the 1-amido-1-phenylalkanes the base peak appeared at m/z 106 [[graphic omitted]H₂CHPh] for (3a–c), and m/z 99 [ĊH₂Ph] for (3d).