Chromium,pentacarbonyl(methoxyphenylmethylene)-, (OC-6-21)-

Base Information

• Chemical Name: Chromium,pentacarbonyl(methoxyphenylmethylene)-, (OC-6-21)-
• CAS No.: 27436-93-7
• Molecular Formula: C13H8 Cr O6
• Molecular Weight: 312.199
• Mol file: 27436-93-7.mol

Synonyms:Chromium,pentacarbonyl(a-methoxybenzylidene)-(7CI,8CI); Benzene, (methoxymethyl)-, chromium complex; (a-Methoxybenzylidene)chromiumpentacarbonyl; Pentacarbonyl(methoxyphenylcarbene)chromium;Pentacarbonyl(methoxyphenylmethylene)chromium; Pentacarbonyl(a-methoxybenzylidene)chromium;Pentacarbonyl[methoxy(phenyl)methylidene]chromium; Phenylmethoxycarbenechromiumpentacarbonyl; [Methoxy(phenyl)carbene]pentacarbonylchromium(0)

Chemical Property of Chromium,pentacarbonyl(methoxyphenylmethylene)-, (OC-6-21)-

Chemical Property:

• PSA: 0.00000
• LogP: 0.54990

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Chromium,pentacarbonyl(methoxyphenylmethylene)-, (OC-6-21)-

There total 21 articles about Chromium,pentacarbonyl(methoxyphenylmethylene)-, (OC-6-21)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

trimethoxonium tetrafluoroborate (420-37-1) + phenyllithium (591-51-5) + chromium(0) hexacarbonyl (199620-14-9,13007-92-6) → pentacarbonyl(1-methoxybenzylidene)chromium(0) (27436-93-7)

Guidance literature:

In diethyl ether; water; N2-atmosphere; dropwise addn. of equimolar amt. PhLi to Cr-complex soln.(in ether) at room temp., stirring for 40 min, solvent removal (vac.), dissoln. in H2O, portionwise addn. of OMe3BF4 to acidic reaction; extn. of aq. layer into ether, solvent removal (vac.), chromy. (SiO2, CH2Cl2/petroleum ether=1:9);

DOI:10.1016/S0022-328X(96)06764-2

Reference yield: 65.0%

phenyllithium (591-51-5) + chromium(0) hexacarbonyl (199620-14-9,13007-92-6) + methyl trifluoromethanesulfonate (333-27-7) → pentacarbonyl(1-methoxybenzylidene)chromium(0) (27436-93-7)

Guidance literature:

In diethyl ether; N2-atmosphere; addn. of PhLi (1 equiv.) to soln. of Cr(CO)6 at 0°C, warming to room temp., stirring for 1 h, cooling (0°C), addn. of MeOTf (3 equivs.), stirring for 20 min at room temp.; pouring onto satd. aq. soln. of NaHCO3, extn. (hexane, 3x), drying (Na2SO4), evapn., chromy. (SiO2, hexane); NMR-spectroscopy;

DOI:10.1021/om9905198

Reference yield: 57.0%

Methyl fluorosulfonate (421-20-5) + phenyllithium (591-51-5) + chromium(0) hexacarbonyl (199620-14-9,13007-92-6) → pentacarbonyl(1-methoxybenzylidene)chromium(0) (27436-93-7)

Guidance literature:

In diethyl ether; cyclohexane; To a suspension of Cr(CO)6 in Et2O under N2 at 0°C is added PhLi in cyclohexane over 10 min, soln. turns to dark yellow, soln. is stirred for 1 h at 25°C, then methyl fluorosulfonate is added, stirring of soln. for 12 h at 25°C.; mixture is poured into a H2O/Et2O mixture, drying of ether layer over Na2SO4, solvent removal, resulting orange solid is dissolved in hexane, chromy.;

DOI:10.1016/0022-328X(89)80121-4

upstream raw materials:

pentacarbonyl((phenyl)(tetramethylammonio)oxycarbene)chromium⁽⁰⁾

diphenylmethylsulfonium tetrafluoroborate

methoxy(phenyl)diazirine

chromium⁽⁰⁾ hexacarbonyl

Refernces

• 1、 Bernasconi, Claude F.,Flores, Francis X.,Gandler, Joseph R.,Leyes, Aquiles E.. "Physical organic chemistry of transition metal carbene complexes. 4. Kinetics and equilibria of methoxide ion addition to [methoxy(phenyl)carbene]pentacarbonylchromium(0) and [methoxy(phenyl)carbene]pentacarbonyltungsten(0)". . p. 2186 - 2193. Retrieved 1994.
• 2、 Toomey, Laurence M.,Atwood, Jim D.. "Abstraction of methyl from neutral Fischer-type carbene complexes: A new site for nucleophilic attack". . p. 490 - 493. Retrieved 1997.
• 3、 Yang, Dominic C.,Dragisich, Vera,Wulff, William D.,Huffman, John C.. "Insertion Reactions of Chromium-Carbene Complexes with Organic Nitriles and a Diastereoselective Alkylation of a Resulting Imino-Carbene Complex". . p. 307 - 309. Retrieved 1988.
• 4、 Harrity, Joseph P. A.,Kerr, William J.,Middlemiss, David,Scott, James S.. "Total synthesis of parvaquone and the serendipitous discovery of a novel chromium-mediated method for β-lactone formation". . p. 219 - 227. Retrieved 2007/10/03.