53920-89-1Relevant 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.
CHEMISTRY OF DIENES AND THEIR DERIVATIVES. XVI. DIRECTION OF ADDITION OF HYDROGEN CHLORIDE TO α-CHLOROISOPRENE (1-CHLORO-3-METHYL-1,3-BUTADIENE)
Tatevosyan, N. Ts.,Mkryan, G. G.,Kaplanyan, E. E.,Mkryan, G. M.
, p. 52 - 54 (2007/10/02)
The 4,3-addition product is formed preferentially together with the 4,1-, 1,4-, and 1,2-addition products during the hydrochlorination of α-chloroisoprene (1-chloro-3-methyl-1,3-butadiene) with concentrated hydrochloric acid at room temperature with and without the presence of cuprous chloride.During low-temperature (-15 deg C) chlorination of a mixture of 1,3-dichloro-3-methyl-1-butene and 1,1-dichloro-3-methyl-2-butene in the presence of tert-butylpyrocatechol the anomalous chlorination product 3,4,4-trichloro-2-methyl-1-butene is mainly formed. 1,3-Dichloro-3-methyl-1-butene is not chlorinated under these conditions.
