132409-98-4Relevant articles and documents
Solvolysis Rates and β-Deuterium Secondary Kinetic Isotope Effects of Some Tertiary and Secondary Alk-5-enyl Derivatives. Evidence for ?-Participation
Orlovic, Mirko,Borcic, Stanko,Humski, Kresimir,Kronja, Olga,Imper, Vera,et al.
, p. 1874 - 1878 (1991)
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.