1476045-32-5Relevant academic research and scientific papers
Silicon acceleration of a tandem alkene isomerization/electrocyclic ring-opening of 2-methyleneoxetanes to α,β-unsaturated methylketones
Farber, Elisa,Rudnitskaya, Aleksandra,Keshipeddy, Santosh,Lao, Kendricks S.,Gascon, Jose A.,Howell, Amy R.
, p. 11213 - 11220 (2013/12/04)
The first rearrangement of 2-methyleneoxetanes to α,β-unsaturated methylketones is reported. It is proposed that when these substrates are heated, the corresponding oxetenes are formed and subsequently undergo electrocyclic ring-opening to methyl vinylketones. In particular, α-silyl-α,β-unsaturated methylketones were isolated in moderate to high yields and with high stereoselectivities. Based on the proposed mechanism, density functional theory explains the differential kinetics and stereoselectivities among substrates.
