STUDIES IN ALKYLATION .2. REACTIONS OF EPOXYALKYL BROMIDES

Alkylation reactions of the bifunctional ω-bromo-1,2-epoxy alkanes have been found to be markedly dependent upon the solvent and the nature of the nucleophile. In alcoholic media, compounds which generate an anion with a localized electron pair react by opening the oxirane ring to give β-hydroxy-ω-bromoalkyl derivatives. In aprotic solvents, these same compounds react by displacement of bromide ion to give epoxy alkyl derivatives. Compounds which generate anions with a delocalized electron pair react exclusively by displacement of bromide ion. Subsequent cyclization reactions may occur in alcohol if the initial product can be converted into an anion and if the proper spatial relationship exists between the epoxy group and the nucleophilic carbon. © 1969, American Chemical Society. All rights reserved.