16403-42-2Relevant 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 (2014/03/21)
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
On the alkylation of Ph3PCHP(O)Ph2: Formation and crystal structures of neutral and cationic addition compounds
Petz, Wolfgang,Neumüller, Bernhard
, p. 1218 - 1224 (2015/04/27)
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(OAlBr3)Ph2][AlBr4] (9). Small amounts of resultant proton bridged [H{Ph2(O)PCH(Me)PPh3}2][I3]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)Ph2 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.
