Synthesis and X-ray structures of new phosphorus-selenium heterocycles with an E-P(Se)-E′ (E, E′ = N, S, Se) linkageDedicated to the memory of Pascal Le Floch.This article is part of a themed issue on Main group chemistry.CCDC reference numbers 752125-752128. For crystallographic data in CIF or other electronic format see DOI: 10.1039/b9nj00570f

Refluxing a toluene solution of Woollins' reagent, WR , with difunctional aromatic substrates (aryldiamines and aryldithiols) leads to a series of novel five- to seven-membered heterocycles 2a-e , 4a , 4b and 6a-c with an E-P(Se)-E′ (E, E′ = N, S, Se) linkage in 7-98% isolated yields. This method offers a new approach to the library of phosphorus-selenium heterocyclic compounds. All new compounds have been characterized by IR, 1 H, 13 C, 31 P, 77 Se NMR, mass spectrometry and elemental analysis or accurate mass measurement. Four representative X-ray structures are reported. Simple routes to new 5-7 membered P-Se heterocycles have been developed.