Diphenyl trimethylamine

Selective reduction of the cyclopropenone carbonyl group to a CH2 group has been described for diphenyl cyclopropenone utilizing its protonation product 294 or the diphenyl chloro cyclopropenium cation 292, which yielded 1,2-diphenyl-A1,2-cyclopropene (293) on treatment with trimethylamine borane210 ... 

DIHYDROXYLATION Osmium tetroxide-Dihydroquinine acetate. Osmium tetrox-ide-Diphenyl selenoxide. Osmium tetroxide-Trimethylamine N-oxide-Pyiidine. Thallium(l) acetate-iodine. Triphenylmethylphosphonium permanganate. 

Several j3-sultones are claimed to be formed by treatment of alkenes with sulfuric acid or by heating alkenesulfonic acids. Treatment of 2,2-dimethyl-1,1-diphenyl-1-propanol with concentrated sulfuric acid at room temperature is said to give 3-(l,l-diphenylethyl)-3-methyl-l,2-oxathietane 2,2-dioxide (96% yield). Treatment of sodium 3-bromo-2-hydroxybutanesulfonate with phosphorus trichloride is reported to give a low yield of 4-(l-bromoethyl)-l,2-oxathietane 2,2-dioxide.1,2-Oxathietane 2,2-dioxide is suggested as an intermediate in the reaction of /3-hydroxyethanesulfonyl chloride with trimethylamine to give the zwitterion 502. The first four-membered monocycUc sulfurane oxides 502a have been reported. 

Sodium permanganate and, especially, osmium tetroxide oxidize sulfoxides to sulfones but do not oxidize sulfides [837]. When a mixture of equimolar amounts of diphenyl sulfide, diphenyl sulfoxide, and osmium tetroxide is refluxed in ether for 48 h, the sulfoxide is oxidized in 96% yield to the sulfone, whereas the sulfide is completely recovered [837], Certain unsaturated sulfoxides treated with a catalytic amount of osmium tetroxide and trimethylamine oxide as a reoxidant are not only oxidized to sulfones but also hydroxylated at the double bond. The sulfoxide group exerts a steric influence in the hydroxylation two stereoisomers of a sulfoxide yield, by syn hydroxylation, two different stereoisomeric diols (equation 580) [1102]. 

As has been observed previously for Os3(CO)9(/ 3-77 77 t) -C6H6), the coordination mode of the [2.2]-paracyclo-phane ligand in Ru3(CO)9(jU3- 7 77 77 -Ci6Hi6) can be adjusted to a terminal mode by reaction with diphenyl-acetylene in the presence of trimethylamine-A -oxide the alkyne caps the triruthenium face in the place of the arene. When the reaction is conducted thermally in the absence of trimethylamine-W-oxide, additional products are also observed, including a related compound formed by insertion of a CO ligand into the alkyne-metal bond as shown in Scheme 3. 

Diphenyl phosphorochloridite allowed to react with 25%-excess isocyanic acid (prepared by cracking isocyanuric acid at 600 ) in ether in the presence of trimethylamine diphenyl phosphoro (isocyanatidite). Y 70%. F. e. and reactions, such as prepn. of acylisocyanates from carboxylic acid chlorides in pyridine, s. P. R. Steyermark, J. Org. Chem. 28, 586 (1963). 

Diphenylcyclopropene may be made either by dehydrochlorination of l chloro-1,2-diphenyl cyclopropane,or by reduction of the chlorodiphenyl-cyclopropenium ion with trimethylamine-borane in the presence of DMF. Although derivatives of cyclopropenone have been isolable as pure compounds for a number of years, the parent compound has been known only in solution until recently. It has now been purified and shown to have an unusually high b.p. (30 C, 0.45 Torr). It is stable only below its m.p. (—29 to —28°C) and polymerizes at room temperature. 

---