ChemInform Abstract: Simplified Method of Ascertaining Steric Effects in Electrophilic Addition Reactions. A Comparison of Bromination, Oxymercuration, and Hydroboration.

ChemInform Abstract

Correlations of ionization potentials (IP's) vs. relative reactivities of alkenes toward bromination (Br2), oxymercuration (Hg(OAc)₂), and hydroboration (9-BBN: 9-borabicyclo(3.3.1)nonane) show very good (r = 0.83) to excellent (r = 0.98) agreement. The use of alkenes such as (I) and (II) having a broad range of steric requirements and electronic effects reveals that bromination is independent of steric effects while oxymercuration and hydroboration each exhibit a natural separation into sterically similar groups, within which alkene IP's correlate with relative reactivity.