Table 1. XPS Results for the Optimization of the Alkylation/Charge–Neutralization Reaction on 2, via Either the Sodium Salt (a–d) or the Protected Acid (e–h) of the Indicated Alkyl halides (See Figure S3).
reactant | conversiona (%) | |
---|---|---|
a | sodium iodoacetate | 87 |
b | sodium bromoacetate | 54 |
c | sodium bromoethane sulfonate | 74 |
d | sodium bromopropane sulfonate | 70 |
e | tert-butyl iodoacetate + deprotection | 85 |
f | tert-butyl bromoacetate + deprotection | 93 |
g | methyl iodoacetate + deprotection | 79 |
h | methyl bromoacetate + deprotection | 77 |
Based on conversion to quaternary amine as measured by XPS N 1s narrow scans.