85977-94-2Relevant academic research and scientific papers
STUDIES ON THE STEREOCHEMISTRY OF ADDITION REACTIONS OF CYCLOHEXANONES. A DICHOTOMY IN SUBSTITUENT EFFECT DEPENDING ON REACTION CONDITIONS.
Maio, Giorgio Di,Li, Weimin,Vecchi, Elisabetta
, p. 4891 - 4896 (1985)
The stereochemistry of addition reactions of 4-t-Bu, 4-OMe an 4-Cl cyclohexanones, determined under seven different reaction conditions is described.A dichotomy in the substituent influence on stereochemistry is outline and discussed suggesting that it pa
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.
