90108-98-8

Upstream product

• 2579-22-8 Phenylpropargyl aldehyde 
• 15226-74-1 dicobalt octacarbonyl 
• 1515868-45-7 μ-η2-(3-phenyl-2-propynal propylene glycol acetal)dicobalthexacarbonyl 
• 6142-95-6 phenylpropargyl aldehyde diethyl acetal 
• 1515868-29-7 μ-η2-(3,3-diisopropoxy-1-phenyl-1-propyne)-dicobalthexacarbonyl 

Downstream Products

• 126937-72-2 2-(1-Hydroxy-3-phenyl-prop-2-ynyl)-cyclohexanone 
• 124069-78-9 μ-η2-(3,3-dimethoxy-1-phenyl-1-propyne)-dicobalthexacarbonyl 
• 163461-71-0 Co₂(CO)6(C₆H₅CCCH₂OH) 
• 126937-72-2 2-(1-Hydroxy-3-phenyl-prop-2-ynyl)-cyclohexanone 

Relevant academic research and scientific papers

Diastereoselective addition of allyl- And crotylstannanes to dicobalt-complexed acetylenic aldehydes

In an endeavor to utilize metal carbonyl complexes of acetylenic aldehydes and ketones to control the stereoselectivity of nucleophilic acyl addition, the dicobalt hexacarbonyl and dicobalt pentacarbonyl(triphenylphosphine) complexes of 3-phenylpropynal and 2-hexynal were conveniently prepared. Crotyl transfer from either (E)- or (Z)-crotyltributylstannane to Co2(CO) 6-complexed 3-phenylpropynal and 2-hexynal produced 3,4-disubstituted-1,5-enynes with high syn diastereoselectivity. Allyl and 2-methylallyl transfer to Co2(CO)5PPh3- complexed aldehydes was also accomplished with high yields and diastereoselectivities. In all cases, decomplexation of the metal carbonyl moiety was effected, selectively, under very mild oxidative conditions. Exchange of a CO by PPh3 led to decreased overall reactivity. Two competing kinetic processes were observed: stereoselective allylation was observed at low temperature, but at higher temperatures, the first formed allylic alcohol preferentially underwent elimination leading to dienynes.

Cascade reaction including a formal [5?+?2] cycloaddition by use of alkyne-Co2(CO)6 complex

A new cascade reaction including formal [5 + 2] cycloaddition was developed. Treatment of homocinnamyl alcohol and Co2(CO)6-complexed arylpropynal with BF3·OEt2 resulted in the generation of hydrobenzocyclohepta

Radical reactions of the cobalt-complexed propargyl acetals: Inter- and intramolecular variants

Propargyl acetals are used as a new type of substrate in cobaltocene-induced radical reactions stereodirected by a π-bonded Co 2(CO)6 metal core. The experimental protocol involves treatment of the cobalt-complexed acetals with triflic anhydride, an in situ generation of ionic propargyl triflates, and a single-electron, low-temperature reduction of α-alkoxy-stabilized, Co2(CO)6-complexed propargyl cations. Inter- and intramolecular reactions provide a facile access to polyfunctional, topologically diverse 3,4-dialkoxy-1,5-alkadiynes and 3,4-dialkoxy-1,5-cyclodecadiynes with a predominant formation of the respective d,l-diastereomers (73-100% d,l). The stereo- and chemoselectivities are found to be dependent upon the (1) bulkiness of the gamma substituent (1,3-steric induction; d,l- 73-100%), (2) presence of a phosphorus ligand altering the π-bonded metal core (axial ligand induction; d,l- 91-97%), and (3) steric hindrance created by an alpha alkoxy group (1,1-steric induction; d,l- 83-92%).