The facile synthesis of organophosphorusc ompoundsi so fg reat importancef or the development of new synthetic methods by using air-stable sourceso fp hosphorus. In this respect, as ynthetic method that is based on ar eductiver earrangementa nd is capable of converting airstable pentavalent phosphorusc ompounds into reactive trivalent phosphorus compoundsi sapowerful tool. Tetraphe-nyldiphosphine disulfide, which is as helf-stable solid, was the focus of this study,a nd it was shown to undergo reductive rearrangement to trigger the bisthiophosphinylation of av ariety of alkenes,s uch as terminal, cyclic, internal, and brancheda lkenes,1 ,3-dienes,a nd terminal alkynes when exposed to light withoutany catalyst, base, or additive.Scheme1.Reductive rearrangement of TMDPO anddiphosphine disulfide.[a] Y.

The photoinduced reactions of tetraphenyldiphosphine disulfide with a range of organic dichalcogenides successfully afforded a series of phosphorus(V)−chalcogen interelement compounds via a radical process. The relative reactivities of the organic dichalcogenides (i.e., (PhS) 2 , (PhSe) 2 , and (PhTe) 2 ) toward the P III or P V groups in the diphosphine analogues under light were investigated in detail, and a convenient method was developed to form P−S or P−Se interelement compounds from tetraphenyldiphosphine disulfide and (PhS) 2 or (PhSe) 2 upon photoirradiation. Furthermore, the relative photochemical properties and reactivities of tetraphenyldiphophine (P− P interelement compound) and its analogues toward photoinduced radical addition reactions were also discussed. The formed P−E (E = S, Se) interelement compounds could be utilized for ionic reactions, and they could be transformed into various phosphine reagents via one-pot processes.

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This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.

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