90674-71-8Relevant articles and documents
Preparation and Reactivity of New β-Nitrogen-Functionalized Vinylic Organolithium Compounds from Secondary Aliphatic Allylamines
Barluenga, Jose,Canteli, Rosa-Maria,Florez, Josefa
, p. 602 - 606 (2007/10/02)
Two new types of β-nitrogen-functionalized vinylic organolithium compounds have been prepared from secondary aliphatic allylamines through the temporary silylation of the amino group.The monoanionic intermediates 4, stable at -80 deg C, are generated by a bromine-lithium exchange reaction and the dianionic derivatives 2, stable at room temperature, by a tin-lithium transmetalation reaction.Both types of organolithium compounds react with different electrophiles giving functionalized allylamines 7 and 10-27.Moreover, dianionic derivatives 30,33 can be prepared directly by bromine-lithium exchange when the β-elimination reaction of hydrogen bromide in the lithium 2-bromoallylamide is structurally hindered.Additionally, a novel type of anionic 1,3-rearrangement of a trimethylsilyl group from nitrogen to carbon is described.