1334232-88-0Relevant academic research and scientific papers
Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions
Barraza, Scott J.,Denmark, Scott E.
supporting information, p. 2891 - 2895 (2017/10/06)
Alkylation of 2-bromoaniline with benzyl bromide under ostensibly basic N-alkylation conditions resulted in migration of bromine from the 2- to the 4-aryl position. Herein we report our studies to elucidate the mechanism of this rearrangement with the objective of suppressing this unexpected outcome. We find that careful choice of reagents is critical, and that this behavior may be extrapolated to alkylation reactions of electron-rich bromo- and iodoanilines in general.
The photophysics of pyridine-derivatized ortho-, meta-, and para-dibutylamino cruciforms
Hinderer, Florian,Bunz, Uwe H. F.
supporting information, p. 8490 - 8496 (2013/07/19)
The photophysical properties of a series of para-substituted donor-acceptor cruciform fluorophores (p1-4) were investigated and compared with their meta and ortho isomers (m1-4 and o1-4). The structural variations were found to have a significant effect o
Titanium-mediated amination of Grignard reagents using primary and secondary amines
Barker, Timothy J.,Jarvo, Elizabeth R.
, p. 8325 - 8328 (2011/10/31)
Make it, then break it: N-chlorosuccinimide (NCS) was employed as the oxidant in the synthesis of aniline derivatives using the title transformation (see scheme). Functionalization was well tolerated on both the amine and Grignard reagent. An androgen receptor agonist and several analogues were synthesized to demonstrate the utility of this method.
