85977-98-6Relevant academic research and scientific papers
Facile synthesis of N-substituted amides from alcohols and amides
Okada, Iku,Chiba, Kazuhiro,Kitano, Yoshikazu
, p. 1069 - 1075 (2013/06/05)
A facile and versatile method for preparing N-substituted amides from alcohols and amides using a Bronsted acid and an alkali metal halide has been developed. Treatment of tertiary alcohols and amides in the presence of an alkali metal halide or methanesulfonic acid in trifluoroacetic acid at elevated temperature afforded the corresponding N-substituted amides in moderate to high yields. Tertiary alcohols with various functional groups such as ether, ester, imide, carbamate, and halogen groups were tolerated under these conditions. This method can be used for the efficient and practical synthesis of various N-substituted formamides without the use of unmanageable cyano compounds. Georg Thieme Verlag Stuttgart New York.
STERIC AND KINETIC EFFECTS OF CHANGING SOLVENT AND REAGENT IN GRIGNARD REACTIONS ON SOME 4-SUBSTITUTED CYCLOHEXANONES
Cianetti, Claudia,Maio, Giorgio Di,Pignatelli, Vito,Tagliatesta, Pietro,Vecchi, Elisabetta,Zeuli, Errico
, p. 657 - 666 (2007/10/02)
The stereochemistry and relative rates of Grignard reactions on some 4R-substituted cyclohexanones (R = tBu, Me, OMe, CO2Me, OCOPh and Cl) have been determined under two separate reaction conditions (MeMgI in C6H6 and MeMgCl in THF).The results of our studies indicate that substrates containing an ester group have a higher reaction order in Grignard reactant than other groups when reactions were carried out in the aromatic solvent.The same is not true for reactions carried out in THF.Both stereochemical product ratios and relative reaction rates are better understood assuming that compounds containing a polar group (OMe and Cl at least) react via a transition state possessing that group in the axial conformation.
