DBU-promoted regioselective HBr-elimination of vicinal dibromides: effects of the adjacent oxygen and/or other heterofunctional groups

TETRAHEDRON

卷:70

Article

Kutsumura, Noriki^1,2  Toguchi, Shohei¹  Iijima, Masatoshi¹  Tanaka, Osamu¹  Iwakura, Izumi³  Saito, Takao¹ 

[1] Tokyo Univ Sci, Fac Sci, Dept Chem, Shinjuku Ku, Tokyo 1628601, Japan

[2] Univ Tsukuba, Int Inst Integrat Sleep Med WPI IIIS, Tsukuba, Ibaraki 3058577, Japan

[3] JST, PRESTO, Kawaguchi, Saitama 3320012, Japan

关键词: Regioselectivity;    Electronegativity;    Elimination;    Neighboring-group effects;    DBU;   

DOI  :  10.1016/j.tet.2014.08.041

来源: Elsevier

【 摘 要 】

DBU-promoted HBr-eliminations of a variety of vicinal dibromides having an adjacent heteroatom (F, O, or N) under mild basic conditions and relevant theoretical calculations were carried out. These HBr-eliminations proceeded more or less regioselectively, and all associated calculation results agreed with the experimental facts. This work suggests that the HBr-elimination selectivity is an effect of the electronegativity of the neighboring heteroatoms themselves rather than the electron-withdrawing effects of the entire heterofunctional group. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

Free