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oai:ojs.www.eurjchem.com:article/405 2011-06-30T10:44:15Z eurjchem:ART driver

Detailed analysis for the solvolysis of isopropenyl chloroformate D’Souza, Malcolm John Shuman, Kevin Edward Omondi, Arnold Ochieng Kevill, Dennis Neil Solvolysis Grunwald-Winstein equations Isopropenyl chloroformate Chlorocarbonate Addition-elimination Ionization The specific rates of solvolysis (including those obtained from the literature) of isopropenyl chloroformate (1) are analyzed using the extended Grunwald-Winstein equation, involving the NT scale of solvent nucleophilicity (S-methyldibenzothiophenium ion) combined with a YCl scale based on 1-adamantyl chloride solvolysis. A similarity model approach, using phenyl chloroformate solvolyses for comparison, indicated a dominant bimolecular carbonyl-addition mechanism for the solvolyses of 1 in all solvents except 97% 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). An extensive evaluation of the outcomes acquired through the application of the extended Grunwald-Winstein equation resulted in the proposal of an addition-elimination mechanism dominating in most of the solvents, but it is proposed that a superimposed unimolecular (SN1) type ionization is making a significant contribution in 97-70% HFIP, and 97% 2,2,2-trifluoroethanol (TFE). Atlanta Publishing House LLC 2011-06-30 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion application/pdf https://www.eurjchem.com/index.php/eurjchem/article/view/405 10.5155/eurjchem.2.2.130-135.405 European Journal of Chemistry; Vol. 2 No. 2 (2011): June 2011; 130-135 2153-2257 2153-2249 eng https://www.eurjchem.com/index.php/eurjchem/article/view/405/PDF