1374336-85-2Relevant academic research and scientific papers
P=C bonds as building blocks for three- and four-membered heterocyclic cations: Synthesis, structures and mechanistic studies
Bates, Joshua I.,Gates, Derek P.
, p. 1674 - 1683 (2012)
The activation of the P=C bond of phosphaalkenes with electrophiles is investigated as a means to prepare and characterize unusual organophosphorus compounds. Treatment of RP=CHtBu (1 a: R=tBu; 1 b: R=1-adamantyl) with HOTf (0.5 equiv) affords diphosphiranium salts [RP-CHtBu-PR (CH2tBu)]OTf ([2 a]OTf and [2 b]OTf), each containing a three-membered P2C ring. In contrast, the addition of MeOTf (0.5 equiv) to either 1 a or 1 b affords diphosphetanium salts [RP-CHtBu-P(Me)R-CHtBu]OTf ([3 a]OTf and [3 b]OTf) containing four-membered P2C2 heterocycles. The phosphenium triflate [tBuP(CH2tBu)]OTf ([5 a]OTf) and methylenephosphonium triflate [tBu(Me)P=CHtBu]OTf ([7 a]OTf) are identified spectroscopically as intermediates in the formation of [2 a]+ and [3 a]+, respectively. The phosphenium triflate intermediate can be trapped with 2-butyne to afford phosphirenium salt [MeC=CMe-tBuPCH 2tBu]OTf ([6 a]OTf). Copyright
