Ontology highlight
ABSTRACT:
SUBMITTER: Barraza SJ
PROVIDER: S-EPMC5997282 | biostudies-literature | 2017 Dec
REPOSITORIES: biostudies-literature
Barraza Scott J SJ Denmark Scott E SE
Synlett : accounts and rapid communications in synthetic organic chemistry 20170821 20
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. ...[more]