On treatment with bases, the C3-C4 bonds of the 3-substituted 4-(1-iminoethyl)- or 4-acetylazetidin-2-ones 8f, 8g and 8i are cleaved heterolytically to afford, depending on the nature of the 3-substituent, ring expansion or other products (14, 19 and 27, respectively). Related compound 8h undergoes a base-induced ring transformation to afford compound 23 only after oxidation to the stereoisomeric disulfanes 20. Compound 8d, when treated with HCl, undergoes a ring transformation to pyrrolidin-2-one 32.
在碱的处理下,3-取代的4-(1-亚胺基乙基)-或4-乙酰基氮杂环戊二酮8f、8g和8i的C3-C4键被杂离子裂解,产生依赖于3-取代基性质的环扩张或其他产物(分别为14、19和27)。相关的化合物8h在氧化为立体异构二硫醚20后,经过碱诱导的环转化,只能得到化合物23。化合物8d在受到HCl处理时,会发生环转化,生成吡咯烷-2-酮32。