Studies on the molecular toxicology of buta-1,3-diene and isoprene epoxides.
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.
Department of Chemistry, University of Newcastle upon Tyne, United Kingdom.
C
C
Bleasdale
R D
RD
Small
W P
WP
Watson
J
J
Wilson
B T
BT
Golding
D002070:Butadienes / Q000378:metabolism / Q000633:toxicity*; D004247:DNA / Q000187:drug effects; D004852:Epoxy Compounds / Q000378:metabolism / Q000633:toxicity*; D045782:Hemiterpenes; D006801:Humans; D010420:Pentanes
D002070:Butadienes; D004852:Epoxy Compounds; D045782:Hemiterpenes; D010420:Pentanes; C005059:isoprene; C024370:3,4-epoxy-1-butene; D004247:DNA