134878-49-2Relevant academic research and scientific papers
REACTIONS OF α,α-DIMETHYLALLYL ALCOHOL WITH POSITIVE CHLORINATION REAGENTS: SYNTHESIS OF 1-CHLORO-2,3-EPOXY-3-METHYLBUTANE
Bentley, Stuart,Goosen, Andre,Laue, Hugh A. H.,Taljaard, Benjamin
, p. 1566 - 1590 (2007/10/02)
Various approaches to the synthesis of the title compound, 1-chloro-2,3-epoxy-3-methylbutane, via the chlorination reactions of α,α-dimethylallyl alcohol have been followed.Attempted one-step synthesis of the epoxide from the substrate alcohol with either highly alkaline sodium hypochlorite, or t-butyl hypochlorite in the absence of solvent, gave mediocre yields of epoxide, accompanied by a variety of chlorinated products via mechanistic pathways proposed to involve neighbouring group participation (NGP) of the hydroxyl moiety.Good overall yields of epoxide were obtained in a two step synthesis involving chlorination of the alcohol with chlorine gas in solvent, followed by treatment of the chlorohydrin product with either base or dry silica gel.
