本文研究了2-芳氨基硫酰基苯并咪唑啉、2-芳氨基硫酰基四氢咪唑和2-芳氨基硫酰基三唑啉内盐（N-杂环卡宾衍生的C＋-C-N－和C＋-C-S－两可性双1,3-偶极离子）与烯酮的 [3+2] 环加成反应。反应以高度化学选择性生成C-C-N环加成产物—苯并咪唑啉螺吡咯烷酮、四氢咪唑螺吡咯烷酮和三唑啉螺吡咯烷酮，产率达到58-93%之间。理论计算研究表明，该 [3+2] 环加成反应是分步历程，1,3-偶极离子以C＋-C-N－偶极体与烯酮环化是动力学和热力学均有利的过程。本文通过偶极体与三种不同方法产生的烯酮进行反应对反应历程进行了验证。全文共合成了18个螺吡咯烷酮化合物，所有新化合物均进行了红外、核磁、质谱和元素分析（或高分辨质谱）表征。其中4,4-二甲基-1,3-二苄基-1-苯基螺[苯并咪唑啉-2,3-四氢吡咯]-2-硫羰基-5-酮的结构经过X-ray单晶衍射分析确证。该反应在室温下通常只需半小时即可完成，反应中只观察到C＋-C-N－ 1,3-偶极体与烯酮的 [3+2] 环加成产物，而没有发现C＋-C-S－ 1,3-偶极体反应的产物。这种高效和高度化学选择性反应为合成苯并咪唑啉、四氢咪唑和三唑螺啉螺吡咯烷酮类化合物提供了最直接和有效的方法，而构建这些螺杂环化合物是其它方法不易实现的。

2-Arylthiocarbamoyl benzimidazolium, -imidazolinium and -triazolium inner salts [the ambident C＋-C-N－and C＋-C-S－ 1,3-dipoles derived from N-heterocyclic carbenes] underwent a highly selective [3+2] cycloaddition reaction with ketenes, leading to the formation of C＋-C-N－ cycloaddition products, benzimidazoline-, imidazolidine-, and triazoline-spiro-pyrrolidones, in 58-93% yields. Theoretical calculation suggested a stepwise mechanism for the reaction and indicated that the C＋-C-N－ cycloaddition of the dipoles with ketenes is a both dynamically and thermodynamically favored reaction pathway. The mechanism was supported by the reaction between 2-arylthiocarbamoyl benzimidazolium salt with ketenes generated via three methods. All 18 spiro-pyrrolidone compounds were fully characterized by IR, 1H NMR, 13C NMR, MS and EI or HRMS. The structure of 1,3-dibenzyl-1-phenyl-4,4-dimethylspiro[benzimidazoline-2,3-pyrrolidine]-2-thioxo-5-one was determined by single-crystal X-ray diffraction analysis.The reaction was completed in 30 to 45 minutes and only C＋-C-N－ cycloaddition products were detected. This highly efficient and selective [3+2] cycloaddition reaction affords a powerful and versatile method in constructing novel benzimidazoline-, imidazolidine- and triazoline-spiro-pyrrolidones, which are not easily accessible by other methods.