Tertiary phosphine sulfides

Tertiary phosphine sulfides are generally stable compounds and are not easily oxidised by air, although they can be oxidised by hydrogen peroxide or dilute nitric acid. The analogous tertiary phosphine selenides and tellurides are however, more reactive to oxidation. Similar to the sulfides they can be prepared from the direct reaction of elemental chalcogen with a tertiary phosphine (Equation 1). Tertiary phosphine selenides are also accessible from tertiary phosphines using KSeCN as the selenium source instead of the element itself. 

Unlike the tertiary phosphine and arsine oxides which form a variety of nickel complexes with peculiar properties, tertiary arsine sulfides and, particularly, tertiary phosphine sulfides... 

Tri-n-butyldifluorophosphorane was first obtained upon interaction between tri-re-butylphosphine and hexafluoro-thioacetone dimer.The method described here involves the reaction of tri-n-butylphosphine sulfide with antimony-(III) fluoride. The method is more generally apphcable in the synthesis of difluorophosphoranes from tertiary phosphine sulfides. The only previously reported difluoro-phosphorane, triphenyldifluorophosphorane, was obtained by the reaction of triphenylphosphine or triphenylphos-phine oxide with sulfur(IV) fluoride under autogenous pressure. ... 

Thiophosphinic halides behave differently purely aliphatic members of this series give only tertiary phosphine sulfides with either alkyl or aryl Grignard... 

Tertiary phosphine sulfides were reported as products from the reaction of thiophosphoryl chloride with Grignard reagents in a ratio greater than 1 3 (183,188). However, Kabachnik and Shepeleva discovered in 1949 that diphosphine disulfides can result from this condensation (101). 

A patent indicates that thiophosphinyl halides behave as expected with Grignard reagents tertiary phosphine sulfides are formed (77). 

The enhancement of the catalytic activity by the addition of the third component was observed also with this type of catalyst. Effective third components are tertiary phosphines, sulfides, sulfoxides, quinones and N-chlorosuccinimide. Alcohols, ketones and aldehydes, on the other hand, deactivated the catalyst even in... 

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