A variety of cyclic and acyclic products are reported for reactions of thiocarbonyl compounds with carbenes and their metal complexed derivatives. Electrophilic and nucleophilic carbenes react with non-enolizable thioketones yielding thiocarbonyl ylides or 1,3-zwitterions, respectively, as plausible, reactive intermediates. In most cases, the initially formed intermediates undergo 1,3-electrocyclization yielding respective thiiranes, which, depending on the substitution pattern, are either isolated as final products or extrude elemental sulfur forming substituted ethylene derivatives. In addition, reactive thiocarbonyl ylides formed from α-oxo substituted carbenoids after the thiophilic attack onto the C = S bond undergo competitive 1,3- versus 1,5-dipolar electrocyclization leading to thiiranes or 1,3-oxathioles, respectively. From the point of view of potential practical applications (coordination chemistry, organometallic chemistry, polymer chemistry), zwitterionic hetarylidene dithiocarboxylates accessible as stable 1:1 adducts from the reactions of nucleophilic heterocyclic carbenes (NHCs) with carbon disulfide are of great interest. GRAPHICAL ABSTRACT

中文翻译：

---

硫代羰基化合物与亲电和亲核卡宾及其金属配合物的反应

据报道，硫代羰基化合物与卡宾及其金属络合衍生物的反应有多种环状和非环状产物。亲电和亲核卡宾与不可烯醇化的硫酮反应分别产生硫代羰基叶立德或 1,3-两性离子，作为合理的反应中间体。在大多数情况下，最初形成的中间体经过 1,3- 电环化产生相应的硫杂丙环，根据取代模式，它们要么作为最终产物分离，要么挤出元素硫形成取代的乙烯衍生物。此外，在亲硫性攻击 C = S 键后由 α-氧代取代的卡宾形成的反应性硫代羰基叶立德分别进行竞争性 1,3- 对 1,5-偶极电环化，导致硫杂环烷或 1,3-氧杂硫醇。从潜在的实际应用（配位化学、有机金属化学、聚合物化学）的角度来看，从亲核杂环卡宾 (NHCs) 与二硫化碳的反应中作为稳定的 1:1 加合物可获得的两性离子杂亚芳基二硫代羧酸盐是非常令人感兴趣的。图形概要