1568031-92-4Relevant academic research and scientific papers
On the alkylation of Ph3PCHP(O)Ph2: Formation and crystal structures of neutral and cationic addition compounds
Petz, Wolfgang,Neumüller, Bernhard
, p. 1218 - 1224 (2014)
Ylide Ph3PCHP(O)Ph2 (1) is the hydrolysis product of carbone C(PPh3)2 and reacts with MeI to produce the corresponding salt [Ph3PCH(Me)P(O)Ph2]I (2). Deprotonation of the cation of 2 with K[N(SiMe3)2] in methyl cyclohexane or toluene gives neutral ylide Ph3PCMeP(O)Ph2 (7). Addition of AlBr3 at the oxygen atom of 7 involves simultaneous uptake of a proton along with formation of [Ph3PCH(Me)P(OAlBr 3)Ph2][AlBr4] (9). Small amounts of resultant proton bridged [H{Ph2(O)PCH(Me)PPh3}2][I 3]3 (10) were isolated during attempts to silylate 2 with trimethylsilytriflate; the main product was found to be [Ph3PCH(Me) P(O)Ph2](O3SCF3) (8). In the course of our studies several by-products with cation [Ph3PCH2P(O) Ph2]+ (4 to 6) were obtained. All compounds were characterized by multiple NMR and X-ray analyses. New cationic and neutral compounds were obtained by treating phosphonioylide Ph3PCHP(O)Ph 2 with MeI. The alkylated product can be deprotonated and gives an addition product with AlBr3. Product characterizations were carried out using 31P NMR spectroscopy and single-crystal X-ray diffraction analyses. Copyright
