114059-06-2Relevant academic research and scientific papers
Synthesis of Substituted Cyclooctenones: Substituent Effects in the -Sigmatropic Rearrangement of Divinylcyclobutanols
Miller, Scott A.,Gadwood, Robert C.
, p. 2214 - 2220 (2007/10/02)
From cyclobutanone 1 12 divinylcyclobutanols were prepared.Substituent effects on the rate of oxy-Cope rearrangement to form cyclooctenones were monitored by NMR.Divinylcyclobutanols 2a, 4a, 5a, 6a, and 8a gave first-order rate constants with the rates of rearrangements being in the order 4a 5a 2a 6a 3a 8a.Cyclobutanols 7a, 9a, 10a, and 12a all rearranged too fast to isolate.The steric effects on the rate of rearrangement and the synthetic utility of this methodology are discussed.
