Studies on the molecular toxicology of buta-1,3-diene and isoprene epoxides

Article abstract of DOI:10.1016/0300-483X(96)03458-0

Reactions of ethenyloxirane with amino (RNH₂) and thiol (R'SH) nucleophiles occur by an S(N)2 mechanism involving competing ring cleavage at C-2 and C-3. In contrast, 2-ethenyl-2-methyloxirane reacts with amino (RNH₂) and thiolate (R'S⁺) nucleophiles in methanol by regioselective S(N)2 attack at C-3 ('neo-pentyl' position). However, in pure water or methanol S(N)1 reaction occurs mainly at C-2.