91632-25-6

Upstream product

• 40291-39-2 ethyl 2-(2-methylphenyl)acetate 
• 109-94-4 formic acid ethyl ester 
• 623-73-4 diazoacetic acid ethyl ester 
• 529-20-4 2-methylphenyl aldehyde 

Downstream Products

• 137144-15-1 (rac)-2-(2-methylphenyl)propanoic acid 
• 409359-85-9 2-(2-methylphenyl)propenoic acid ethyl ester 
• 91632-31-4 4-o-Tolyl-2H-isoxazol-5-one 
• 91670-47-2 (Z)-3-(2-Methyl-benzoylamino)-2-o-tolyl-acrylic acid 
• 91632-45-0 2,5-Di-o-tolyl-[1,3]oxazin-6-one 

Relevant academic research and scientific papers

Unusual anion effects in the iron-catalyzed formation of 3-hydroxyacrylates from aromatic aldehydes and ethyl diazoacetate

Due to the lability of one of the CO ligands in irans-[Fe(PNP)(CO) 2Cl]+ this compound is an efficient catalyst for the coupling of a series of aromatic aldehydes with ethyl diazoacetate (EDA), which give, in most cases, selectively 3-hydroxyacrylates rather than β-oxo esters. This reaction is strongly dependent on the nature of the counterion, Whereas with BF4- the reaction proceeds with conversions up to 90%, in the case of the counterions NO3-, CF 3COO-, CF3SO3-, SbF 6-, and BAr'4- [Ar' = 3,5-(CF 3)2C6H3] no reaction took place. In the case of PF6- only up to 20% conversion was achieved. A conceivable mechanism for the coupling of aromatic aldehydes with EDA was established by means of DFT/B3LYP calculations, which allowed the rationalization of both the chemoselectivity and the role of the counterions.