Beilstein J. Org. Chem.2016,12, 245–252, doi:10.3762/bjoc.12.26
Helmut Ritter Monir Tabatabai Markus Herrmann Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-University Duesseldorf, Universitaetsstraße 1, D-40225 Duesseldorf, Germany 10.3762/bjoc.12.26 Abstract We describe the synthesis of bromo-tert-butyloxycarbonyl (Br-t-BOC
, IR, GPC and DSC methods. The kinetics of the deprotection step was followed by 1H NMR spectroscopy. The solvent polarity and neighboring group effects on the kinetics of deprotection are discussed.
Keywords: amino group protection; bromo-tert-butyloxycarbonyl; deprotection; free radical
this in mind, the bromo-tert-butyloxycarbonyl (Br-t-BOC) group represents the first known solvent-polarity sensitive amino-protecting group. As shown in Figure 1, this group is stable in nonpolar solvents because of high activation energy and easily decomposes in a more polar environment because of
PDF
Graphical Abstract
Figure 1:
Schematic representation of a deprotection taking the relatively high polarity of the transition st...