Methyldiphenylphosphine oxide

Enamines.1 This Wittig-Homer reagent (1) is not useful for reactions with ketones because of its basicity. This difficulty is overcome by use of (N-methylani-lino)methyldiphenylphosphine oxide (2), which undergoes Wittig-Homer reactions with a wide variety of ketones as well as aldehydes to give N-methylanilino enamines (3) as a mixture of (E)- and (Z)-isomers. The less stable (Z)-isomers can be isolated by crystallization at low temperature. 

Ohler, E.. and Zbiral. Ei.. Oxidative rearrangement of phosphorus containing tertiary allylic alcohols. Synthesis of (3-oxo-l-cycloalkenyl)phosphonates, -methylphosphonates, -methyldiphenylphosphine oxides and their epoxy derivatives. Synthesis, 357, 1991. 

Methyldiphenylphosphine oxide, (CH3)(CeH5)2PO, may be isolated by the reactions indicated in the following equations — ... 

Lithiated methyldiphenylphosphine oxides bearing an organo-lead, -tin, -antimony, or -tellurium group in the a-position react with carbonyl compounds at low temperatures to give exclusively vinyldiphenylphosphine oxides (e.g. Scheme 39). ... 

An aqueous solution of methyltriphenylphosphonium iodide or chloride is treated with freshly precipitated silver oxide and boiled with water until a filtered test portion of the solution shows no turbidity with silver nitrate. The mixture is then entirely filtered and the filtrate evaporated to dryness on the water-bath. The residue is extracted with ether, the solvent removed and the product crystallised from ether, prisms resulting, M.pt. 110° to 111° C. The oxide has also been prepared by the interaction of diphenylchlorophosphine and sodium methoxide, when it melts at 109° to 110° C., methyldiphenylphosphine occurring as a by-product. When obtained by heating an alcohol solution of methyltribiphenylphosphonium iodide with moist silver oxide, it crystallises in needles, M.pt. 223° to 224<° C. ... 

Methyldiphenylphosphine, CHg(C6H5)2p, occurs when zinc dimethyl is allowed to interact with diphenylchlorophosphine.It is a colourless, refractive oil, B.pt. 284° C., density 1 0784 at 15° C. It has a pungent odour, and is miscible with alcohol or benzene, but insoluble in ether. Oxidation converts it into the corresponding oxide. 

Bis(triphenyltin)dihydridobis(methyldiphenylphosphine)plati-num, see Sn-00474 Bis(triphenyltin)oxide, see Sn-00440 >Bis(triphenyltin) sulfide, Sn-00443 Bis(triphenyltin)telluride, Sn-00446 >Bis(tripropyltin) oxide, see Sn-00339 >Bis[tris(2-methyl-2-phenylpropyl)tin] oxide, see Sn-00473 Bis[tris(pentafluorophenyl)germyl]cadmium, Ge-00271 Bis[tris(pentafluorophenyl)germyl] mercury, Ge-00273 Bis[tris(pentafluorophenyl)germyl] selenide, see Ge-00275 Bis[tris(pentafluorophenyl)germyl] sulfide, see Ge-00274 [Bis[tris(pentafluorophenyl)stannyl]]mercury, Sn-00435 Bis[tris(trifluoromethyl)germanium]oxide, see Ge-00064 Bis[tris[(trimethylsilyl)methyl]stannyl]mercury, Sn-00399 Bromo( 7 -2,4-cyclopentadien-1 -yl)lead, Pb-00035 Bromo( 7 -2,4-cyclopentadien-1 -yl)tin, Sn-00086 Bromodimethylstannane, Sn-00022... 

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