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  • Title: Studies on the molecular toxicology of buta-1,3-diene and isoprene epoxides.
    Author: Bleasdale C, Small RD, Watson WP, Wilson J, Golding BT.
    Journal: Toxicology; 1996 Oct 28; 113(1-3):290-3. PubMed ID: 8901910.
    Abstract:
    Reactions of ethenyloxirane with amino (RNH2) and thiol (R'SH) nucleophiles occur by an SN2 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 SN2 attack at C-3 ("neo-pentyl" position). However, in pure water or methanol SN1 reaction occurs mainly at C-2.
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