92610-71-4Relevant academic research and scientific papers
On the Stereoelectronic Requirements of 1,2-Rearrangements of Vinyl Cations
Collins, Clair J.,Martinez, Antonio Garcia,Alvarez, Roberto Martinez,Aguirre, Juan Arranz
, p. 2815 - 2824 (2007/10/02)
The triflates 8,9,12,17,19, and 23 have been synthesized to investigate their solvolysis products in absol. 2,2,2-trifluoroethanol (TFE) (Table 1).The kinetics of the solvolysis in 50percent ethanol have been measured as well.The rate constants give a straight correlation line when we apply an approximate Taft's equation, from which we deduce that the solvolyses take place by a kc mechanism; one exception is 12, as it reacts with S-O bond cleavage.We also deduce that the value of ρ* does not depend on steric factors.Relations between structure and rearrangement of vinyl cations are discussed.Mechanisms for the formation of reaction products are proposed.
