Application of the Extended Grunwald-Winstein Equation to Solvolyses of n-Propyl Fluoroformate and a Consideration of Leaving Group Effects

Bulletin of the Korean chemical society

Jin Burm Kyong¹  Dong Kook Kim¹  Dennis N Kevill¹  Mi Hye Seong¹ 

关键词: n-Propyl fluoroformate;    Addition-elimination;    Grunwald-Winstein equation;    Leaving group effect;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

Reactions of n-propyl fluoroformate in a variety of pure and binary solvents have been studied at 40.0 oC. The extended (two-term) Grunwald-Winstein equation has been applied to the specific rates of solvolysis of n-propyl fluoroformate. The sensitivities (l = 1.80 �? 0.17 and m = 0.96 �? 0.10) to changes in solvent nucleophilicity and solvent ionizing power and the k_F/k_Cl values are similar to those for solvolyses of n-octyl fluoroformate over the full range of solvents, suggesting that the addition step of an addition-elimination mechanism is ratedetermining. These observations are also compared with those previously reported for the corresponding chloroformate and fluoroformate esters.

【 授权许可】

Unknown