The steric course of the reaction of ethylene oxide with hydrogen halides in the gas phase
Abstract
The steric course of the gas-phase reaction of trans-[2H2]ethylene oxide with HF, HCl, and HBr was investigated in order to test experimentally a mechanistic proposal based on ab initio calculations involving a concerted syn-opening mechanism. In contrast with this proposal the reactions with HCl and HBr take place entirely with anti-opening of the ring to give erythro-2-chloro- and 2-bromo[1,2-2H2]ethanol. The reaction of ethylene oxide with gaseous HF yields only 5% 2-fluoroethanol, 37% dioxan, oligomers and polymers being the main products. An improved method for the conversion of cis- and trans-[2H2]ethylene into the corresponding epoxides is described.
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