How Not to Discover a New Reagent. The Evolution and Chemistry of Woollins' Reagent

Abstract

Abstract:The pathways in research can be complex. This review provides a personal account of the winding scientific and funding road which led to Woollins' Reagent. The synthesis and demonstrative reactions of Woollins' Reagent are summarized.

Preparation and Characterization of Phenyl Phosphine Diselenide – The Monomeric Form of Woollins' Reagent

“…reagent [1,2] (2,4-diphenyl-1,3,2,4-diselenadiphosphetan-2,4-diselenide; 2) has been employed in a variety of selenium atom transfer reactions [3,4] and organic P-Se heterocycle syntheses. [5][6][7] At temperatures above 100°C, 2 has been assumed to dissociate into its monomer phenyl phosphine diselenide (1).…”

Novel organo phosphorus–selenium heteroatom compounds from selenation of diamines

“…8 Reactions of WR with organic substrates range from simple oxygen-selenium exchange to the formation of complex phosphorus-selenium heterocycles as well as surprising phosphorus-selenium-free products. [9][10][11][12][13][14][15][16][17][18][19][20][21] Recently, we reported the synthesis of a series of ammonium phenylphosphonamidodiselenoates and phenylphosphonamidodiselenoic diamides from the selenation of primary/secondary amines. 22 As part of our study into the reactivity of WR towards different organic nucleophiles, we herein report the synthesis of a series of novel diammonium phenylphosphonamidodiselenoates and their derivatives including three representative X-ray structures.…”

Organophosphorus–Tellurium Chemistry: From Fundamentals to Applications

“…[1][2][3][4][5][6] In part, this tardiness can be attributed to the thermal and photochemical lability of phosphorus-tellurium bonds that makes many of these compounds difficult to manipulate. Significantly, there is no tellurium counterpart of the Lawesson's or Woollins' reagents, which contain both bridging (P-E) and terminal P=E (E = S, Se, respectively) functionalities; the latter reagents find wide applications in organic chemistry for the NMR studies of phosphorus-tellurium compounds and, in particular, the magnitude of the one-bond coupling constant 1 J( 31 P, 125 Te) are of considerable interest.…”

“…5,6 In addition, organophosphoruschalcogen compounds are used as pesticides or nerve agents, as precursors for metal chalcogenide thin films or nanoparticles, in metal extraction processes and as lubricant additives. The chemistry of phosphorus-chalcogen compounds has been covered comprehensively in a recent book chapter that deals primarily with sulfur and selenium-containing systems.…”