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Four-membered rings with a P 2 Ch 2 core (Ch=S, Se) and phosphorus in the +3 oxidation state have been synthesized. The utility of these rings as a source of monomeric phosphinidene chalcogenides was probed by the addition of an N-heterocyclic carbene, resulting in a base-stabilized phosphinidene sulfide. Similarly, persistence of the phosphinidene selenide in solution was shown through cycloaddition chemistry with 2,3-dimethylbutadiene at elevated temperatures. The observed reactivity was explained by detailed computational work that established the conditions upon which the P 2 Ch 2 rings can liberate phosphinidene chalcogenides., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)