Notes - Reaction of 1-Bromo-2,3-epoxybutane and 3-Bromo-1,2-epoxybutane with phenol

Epihalohydrins in Organic Synthesis

“…This study clearly illustrated that the nucleophile reacted at the least hindered site. Interestingly, the reaction of both oxiranes 328 and 330 with phenol under basic conditions took place by the same mechanism (Scheme )that is, initial attack of the phenoxide ion at the ring carbon (C3) farthest from the bromomethyl groupthus indicating that not only the steric factor but also the nature of the nucleophile was important in the chemoselectivity of the reaction …”

“…Interestingly, the reaction of both oxiranes 328 and 330 with phenol under basic conditions took place by the same mechanism (Scheme 107) that is, initial attack of the phenoxide ion at the ring carbon (C3) farthest from the bromomethyl groupthus indicating that not only the steric factor but also the nature of the nucleophile was important in the chemoselectivity of the reaction. 319 Interestingly, the reaction of 1-bromo-2,3-epoxy-1-phenylpropane (332a) with several aliphatic amines has been described to form 1-alkyl-3-hydroxy-2-phenylazetidines 336 (Scheme 108). 320,321 A similar reaction of the isomeric 1-bromo-2,3epoxy-1-phenylpropane (332b) with benzylamine, however, afforded only 2-(N-benzylamino)methyl-3-phenyloxirane (337) (Scheme 109).…”