86021-83-2Relevant academic research and scientific papers
Reactions of 3,4,4-Trichloro-3-butenamides with Nucleophiles, II. Thiol- and Amine Adducts of 3,3-Dichloroallenecarboxamides
Roedig, Alfred,Ritschel, Werner
, p. 1595 - 1602 (2007/10/02)
From the reactions of 1 with thiolates and amines only adducts of the intermediate allenes 2 are isolated.With thiolates 1 and 2 give the non-conjugated products 3, which rearrange with strong bases very slowly to yield the conjugated E-compounds 4.In contrast, with sec. amines and tert-butylamine the E-compounds 5 are directly available from 1 and 2.Sterically less pretentious prim. amines yield 1:1 mixtures of E- and Z-isomers 5 and 6, which are transformed into pure Z-adducts 6 by bases.The enamine character of 5e and 6g is elucidated by acid hydrolysis to the β-keto acid derivative 7.
