Ambident Reactivity of Medium-Ring Cycloalkane-1,3-dione Enolates<sup>1</sup>
作者:Glenn S. Thompson、Jerry A. Hirsch
DOI:10.1021/jo971515k
日期:1998.2.1
Cycloalkane-1,3-diones with ring sizes 7-10 have been converted to their enolates and subjected to a variety of ethylation and methylation reagent/solvent systems. The greatest amount of O-alkylation was encountered using ethyl tosylate in HMPA. The O/C alkylation ratios decreased with almost every reagent/solvent system as the ring size was increased. This trend is consistent with greater steric strain in the conjugated enolate resonance contributor, resulting in diminished O-attack as the ring size is increased.
REETZ, M. T.;HEIMBACH, H., CHEM. BER., 1983, 116, N 11, 3702-3707
作者:REETZ, M. T.、HEIMBACH, H.
DOI:——
日期:——
Efficient Synthesis of Diastereomerically Pure Vicinal Diamines: <i>meso</i>-2,3-Bis(methylamino)butane and <i>cis</i>-1,2-Bis(methylamino)cycloalkanes