58822-74-5Relevant academic research and scientific papers
Reactions of 3-Chloro-3-methyl-1-butyne with Hydrogen Chloride: Evidence Against an Electrophilic Addition Reaction
Stammann, Guenter,Rehman, Zillur,Griesbaum, Karl
, p. 3103 - 3111 (2007/10/02)
Reactions of 3-chloro-3-methyl-1-butyne (1) with an excess of anhydrous hydrogen chloride in the liquid phase afforded approx. 16 products.Major product was 1,1,3-trichloro-3-methylbutane (6).In addition, (E)-1,3-dichloro-3-methyl-1-butene (5) and (Z)- and (E)-1,3-dichloro-2-methyl-2-butene (11a, b) were formed in considerable amounts.The expected products of an electrophilic addition to the triple bond, however, were only found in very minute amounts.The formation of the products obtained was rationalized by heterolysis of the C-Cl bond in the substrate 1 and subsequent reactions of the ensuing intermediate mesomeric cation A.
