194654-39-2Relevant academic research and scientific papers
A mechanistically unusual base induced [1,3]-H-shift in homoallylic ethers
Mulzer, Johann,Wille, Gregor,Bilow, Joern,Arigoni, Duilio,Martinoni, Bruno,Roten, Konrad
, p. 5469 - 5472 (2007/10/03)
Upon treatment with NaH in DMF the homoallylic ethers 1a-g and the amine 1h undergo a rearrangement into the trisubstituted (E)-olefins 2a-h. Experiments with isotopically labelled forms of 1a and 1b show that the [1,3]-shift is cleanly intramolecular and proceeds predominantly in the suprafacial mode.
