Abstract
Abstract ArPH2 (Ar=[C6H3(CH2NMe2)2-2,6]) 3 undergoes hydride abstraction on treatment with trityl cation to give the stabilized phosphenium ion [ArPH]+BF4−, 4a. The same cation was prepared by reaction of 3 with BrCCl3 (4b) and also by lithiation of 3 followed by treatment with I2 (4c). ArLi reacts with PX3 (X = Cl or Br) to give the stabilized phosphenium ion [ArPX]+X− which affords 3 by LiAlH4 reduction. In contrast, DIBAL-H reduction of [ArPX]+X− gives [ArPH]+X−. This last reaction constitutes a transformation of a stabilized and functionalized phosphenium ion into a different ion. Confirmation of the structure of these salts was given by single-crystal X-ray diffraction analysis of [ArPH]+PF6− 4e.
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