Journal of Organic Chemistry p. 1874 - 1878 (1991)
Update date:2022-07-29
Topics:
Orlovic, Mirko
Borcic, Stanko
Humski, Kresimir
Kronja, Olga
Imper, Vera
et al.
Tertiary 1,1-dimethylalk-5-enyl chlorides solvolyze in 80percent v/v ethanol with no or moderate rate enhancements attributable to ?-participation.However, secondary β-deuterium kinetic isotope effects (KIE, two deuterated methyl groups) are significantly reduced (kH/kD = 1.22-1.57) relative to the saturated analogues (kH/kD = 1.80), indicating participation of the double bond.Secondary 1-methylalk-5-enyl tosylates show the same trends, i.e., no or very moderate rate enhancements but reduced β-deuterium secondary KIE relative to the saturated analogue.
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