Journal of the Chemical Society. Perkin transactions II p. 1336 - 1340 (1981)
Update date:2022-08-17
Topics:
Bellucci, Giuseppe
Berti, Giancarlo
Bianchini, Roberto
Ingrosso, Giovanni
Moroni, Antonio
The steric course of the gas-phase reaction of trans-<(2)H2>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-(2)H2>ethanol.The reaction of ethylene oxide with gaseous HF yields only 5percent 2-fluoroethanol, 37percent dioxan, oligomers and polymers being the main products.An inproved method for the conversion of cis- and trans-<(2)H2>ethylene into the corresponding epoxides is described.
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