In reactions of propargylic alcohols, RH(HO)CCCH (prop-2-yn-1-ol, meso-but-3-yn-2-ol), with secondary cyclic amines (piperidine, pyrrolidine, morpholine, 1-methylpiperazine, 4-methylpiperidine and meso-3,5-dimethylpiperidine), catalysed by cis-[W(CO)₄(pip)₂], previously unknown diamines containing the tetrahydrofuran ring were isolated in relatively good yield, up to 80%, identified by GC–MS, and characterized by NMR spectroscopy. The new structures were studied by DFT: the ¹H and ¹³C chemical shifts were calculated and compared with those observed experimentally.

中文翻译：

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钨（0）催化的炔丙醇和仲胺反应中不寻常的产物形成：加氢胺化和四氢呋喃环的构建

在炔丙醇的反应中，RH（HO）CC CH（prop-2-yn-1-ol，meso -but-3-yn-2-ol）与仲环胺（哌啶，吡咯烷，吗啉，1-甲基哌嗪，由顺式[[W（CO）₄（pip）₂ ]催化，分离出先前未知的含四氢呋喃环的二胺，产率高达80％，分离出4-甲基哌啶和内消旋3,5-二甲基哌啶）。通过GC–MS进行分析，并通过NMR光谱进行表征。通过DFT对新结构进行了研究：计算了¹ H和¹³ C的化学位移，并将其与实验观察到的进行了比较。