1,3 - 丁二烯和异戊二烯环氧化物的分子毒理学研究。

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

作者信息

Bleasdale C, Small R D, Watson W P, Wilson J, Golding B T

机构信息

Department of Chemistry, University of Newcastle upon Tyne, United Kingdom.

出版信息

Toxicology. 1996 Oct 28;113(1-3):290-3. doi: 10.1016/0300-483x(96)03458-0.

DOI:10.1016/0300-483x(96)03458-0

PMID: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.

摘要

乙烯基环氧乙烷与氨基（RNH₂）和硫醇（R'SH）亲核试剂的反应通过SN2机理进行，涉及C-2和C-3处的竞争性开环。相比之下，2-乙烯基-2-甲基环氧乙烷在甲醇中与氨基（RNH₂）和硫醇盐（R'S⁻）亲核试剂通过在C-3（“新戊基”位置）的区域选择性SN2进攻发生反应。然而，在纯水或甲醇中，SN1反应主要发生在C-2处。