The Influence of Solvent and Metal Ion on the Rate of Reaction of Alkali Metal Borohydrides with Acetone¹

Unexpected effect of alkoxides on the reactivity of sodium borohydrid in the reduction of perfluoropolyether carboxylic esters

“…It seems that protic solvents play an important role since the reduction does not proceed significantly in aprotic media, like diglyme [14]. In hydroxylic solvents, a synchronous mechanism can be postulated involving one (or more) solvent molecules in the transition state as shown in Fig.…”

5‐Substituted 4,5‐Dihydro‐1,2,4‐triazin‐3(2H)‐ones from the Unprecedented Reaction between α‐N‐Protected Amino Acid Hydrazides and NaBH4

“…in MeOH for 20 min. [7] The hydrazide 1da (1.0 equiv.) was subsequently added to the solution thus obtained and the reaction mixture was refluxed for 1 h. After suitable work up, compound 8d was successfully isolated in 90 % yield, but partial racemization (ca.…”

Tetrabutylammonium Borohydride

“…3 Although diborane is probably formed during the reduction of ketones, hydroboration of the carbon-carbon double bond in 6-methyl-5-hepten-2-one was not observed, and the unsaturated alcohol was isolated in good yield. 1 As with other borohydride reductions, 8, 9 there is evidence that the reaction can be assisted by electrophilic catalysis. While not a prerequisite for reduction, the addition of an equivalent amount of ethanol results in an approximate twofold increase in the rate of reduction of cyclohexanone by tetrabutylammonium borohydride in CH 2 Cl 2 .…”