144447-24-5Relevant academic research and scientific papers
The synthesis of (±)-heliotridane and (6S,7S)-dihydroxyheliotridane via sequential hydrogen atom abstraction and cyclisation
Robertson, Jeremy,Peplow, Mark A.,Pillai, Jayasheela
, p. 5825 - 5828 (1996)
Treatment of N-(3-bromo-3-butenyl)pyrrolidine derivatives with tributyltin hydride and AIBN leads to hydrogen atom transfer of the intermediate vinyl radicals to give α-amino radicals which then cyclise stereoselectively yielding pyrrolizidines 1 and 13.
Radical/Polar Annulation Reactions (RPARs) Enable the Modular Construction of Cyclopropanes
Milligan, John A.,Phelan, James P.,Polites, Viktor C.,Kelly, Christopher B.,Molander, Gary A.
, p. 6840 - 6844 (2018)
An annulation process for the construction of 1,1-disubstituted cyclopropanes via a radical/polar crossover process is described. The cyclopropanation proceeds by the addition of a photocatalytically generated radical to a homoallylic tosylate. Reduction of the intermediate radical alkylation adduct (via single electron transfer) furnishes an anion that undergoes an intramolecular substitution. The process displays excellent functional group tolerance, characteristic of proceeding through odd-electron intermediates, and occurs under mild conditions with visible light irradiation.
Ynamide Carbopalladation: A Flexible Route to Mono-, Bi- and Tricyclic Azacycles
Campbell, Craig D.,Greenaway, Rebecca L.,Holton, Oliver T.,Walker, P. Ross,Chapman, Helen A.,Russell, C. Adam,Carr, Greg,Thomson, Amber L.,Anderson, Edward A.
supporting information, p. 12627 - 12639 (2015/09/01)
Bromoenynamides represent precursors to a diversity of azacycles by a cascade sequence of carbopalladation followed by cross-coupling/electrocyclization, or reduction processes. Full details of our investigations into intramolecular ynamide carbopalladation are disclosed, which include the first examples of carbopalladation/cross-coupling reactions using potassium organotrifluoroborate salts; and an understanding of factors influencing the success of these processes, including ring size, and the nature of the coupling partner. Additional mechanistic observations are reported, such as the isolation of triene intermediates for electrocyclization. A variety of hetero-Diels-Alder reactions using the product heterocycles are also described, which provide insight into Diels-Alder regioselectivity.
A practial method for N-alkylation of succinimide and glutarimide
Gesson, J. P.,Jacquesy, J. C.,Rambaud, D.
, p. 227 - 231 (2007/10/02)
Succinimide and glutarimide are N-alkylated in high yield using primary chlorides, bromides or tosylates under solid-liquid PTC conditions (K2CO3, benzene or toluene at reflux, 1percent 18-C-6).Addition of 0.1 eq of KI increases the rate of the reaction for less reactive halides such as 2-bromobutane.Keywords: imide / phase transfer catalysis / N-alkylation
