Attempts to synthesize 2-aryl-2-alkylaminoethyl-1,1-bisphosphonates as potential antiparasitic agents from tetraethyl 2-arylvinylidenebisphosphonate and a suitable alkyl amine led to (E)-N-alkyl-1-arylmethaimines instead of the expected Michael-type adduct. This chemical behavior was not observed when used mercaptans as soft nucleophiles resulting in the corresponding sulfur'-containing Michael-type adducts. A reasonable reaction mechanism was proposed.

中文翻译：

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2-芳基乙烯基二膦酸盐中胺的 Michael 型加成机理研究：通过 Retro-Aza-Michael 型反应消除双膦酸盐


尝试从 2-芳基氨基乙基-1,1-双膦酸盐合成 2-芳基-2-烷基氨基乙基-1,1-双膦酸盐作为潜在的抗寄生剂，结果导致 （E）-N-烷基-1-芳基甲基海胺而不是预期的迈克尔型加合物。当使用硫醇作为软亲核试剂时，未观察到这种化学行为，从而产生相应的含硫迈克尔型加合物。提出了一种合理的反应机制。