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The preparation and isolation of the metalated ylides [Cy 3 PCSO 2 Tol]M (  Cy 1‐M ) (with M = Li, Na, K) are reported. In contrast to its triphenylphosphonium analogue the synthesis of   Cy 1‐M  revealed to be less straight forward. Synthetic routes to the phosphonium salt precursor   Cy 1 ‐ H 2   via different methods revealed to be unsuccessful or low‐yielding. However, nucleophilic attack of the ylide Cy 3 P = CH 2  at toluenesulfonyl fluoride under basic conditions proved to be a high‐yielding method directly leading to the ylide   Cy 1‐H . Metalation to the yldiides was finally achieved with strong bases such as  n BuLi, NaNH 2 , or BnK. In the solid state, the lithium compound forms a tetrameric structure consisting of a (C–S–O–Li) 4  macrocycle, which incorporates an additional molecule of lithium iodide. The potassium compound forms a  C  4 ‐symmetric structure with a (K 4 O 4 ) 2  octahedral prism as central structural motif. Upon deprotonation the P–C–S linkage undergoes a remarkable contraction typical for metalated ylides.

Synthesis, Isolation and Crystal Structures of the Metalated Ylides [Cy 3 P‐C‐SO 2 Tol]M (M = Li, Na, K)