15480-89-4

Basic information

• Product Name: Ethanone, 1-phenyl-, ion(1-), potassium
• CAS NO: 15480-89-4
• Molecular Formula: C8H7O.K
• Molecular Weight: 158.241
• Mol File: 15480-89-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-phenyl-, ion(1-), potassium(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-phenyl-, ion(1-), potassium(15480-89-4)
• EPA Substance Registry System: Ethanone, 1-phenyl-, ion(1-), potassium(15480-89-4)

Safety Data

• Hazardous Substances Data: 15480-89-4(Hazardous Substances Data)

Upstream product

• 98-86-2 acetophenone 

Downstream Products

• 143357-92-0 2-(3-benzothienyl)-1-phenylethanone 
• 95-15-8 Benzo[b]thiophene 
• 60507-03-1 acetophenone-d1 
• 1407511-54-9 Cp₂Ti[OC(=CH₂)Ph](OPh) 
• 154860-74-9 ((C₂H₅)3P)2(CO)Rh(CH₂C(O)(C₆H₅)) 
• 154860-73-8 ((C₂H₅)3P)2(CN(C(CH₃)3))Rh(CH₂C(O)(C₆H₅)) 
• 488780-63-8 trans-[Ru(H)(R-binap)(2,3-diamino-2,3-dimethylbutane)(OC(C₆H₅)=CH₂)] 
• 154859-46-8 (η3-1-phenyl-1-oxoethenyl)bis(triphenylphosphine)rhodium(I) 
• 154859-49-1 (η3-1-phenyl-1-oxoethenyl)bis(triethylphosphine)rhodium(I) 
• 117800-21-2 carbonyl(η1-O-1-phenyl-1-oxyethyl){bis(trimethylphosphine)}rhodium(I) 
• 117800-22-3 carbonyl(η1-O-1-phenyl-1-oxyethenyl){bis(triphenylphosphine)}rhodium(I) 
• 53449-11-9 1,3,4,4-tetraphenyl-3-buten-1-one 
• 117760-41-5 1,4-diphenyl-1,3-pentanedione 
• 117760-45-9 1,4-Diphenyl-hexane-1,3-dione 

Relevant articles and documents

Synthesis of η1 Oxygen-Bound Rhodium Enolates. Applications to Catalytic Aldol Chemistry

Oxygen-bound rhodium enolate complexes are prepared by metathesis of carbonylbis(phosphine)rhodium(I) halides and potassium enolates, 3-6.Rhodium enolates of acetophenone (7), propiophenone (9), ethyl mesityl ketone (10), and ethyl tert-butyl ketone (11) were prepared and fully characterized.Complex 11 condenses with benzaldehyde under a variety of conditions to produce isolable rhodium aldolate complex 12.Cleavage of 12 with trimethylsilyl chloride yields aldol silyl ether and rhodium chloride.Similar treatment of 12 with an enol silane affords the aldol silylether and a rhodium enolate.A catalytic aldol reaction involving enol silanes, silylketene acetals, and benzaldehyde under rhodium catalysis is presented.Deuterium, phosphorus, and carbon NMR were used to demonstrate the intermediacy of rhodium enolates and aldolates in the aldol process and to elucidate the gross mechanistic features of the catalytic cycle.

Nucleophilic Additions to Ketenes by (Trimethylsilyl)lithium and by Enolates

Reaction of t-Bu2C=C=O (5) with Me3SiLi at -78 deg C followed by trapping of the intermediate enolate with Ac2O gave t-Bu2C=C(OAc)SiMe3 (9).Other ketenes gave similar products.Reaction of ketenes PhCR=C=O (R = Me, 13; R = Et, 3) with enolates CH2=C(OLi)R1 (R1 = H, Me, t-Bu, Ph) at -78 deg C followed by warming to 25 deg C and hydrolysis gave vinyl esters PhCHRCO2C(R1)=CH2, along with 10 percent PhCHMeCOCH2COPh for R = Me, R1 = Ph.Under the same conditions the ketenes PhCR=C=O with enolates CH2=C(OK)R1 (R1 = Me, t-Bu, Ph) gave only 1,3-diketones PhCHRCOCH2COR1, but vinyl esters were the major products if the reactions were quenched at -78 deg C.It is proposed that enolates undergo preferential O-acylation by ketenes in a kinetically favored process, but that these intermediates can revert to thermodynamically more stable C-acylated products.