Which reaction of an alkene proceeds with anti-addition?
Too many to list!
Some common ones we often see, are:
- Anti dihydroxylation (acidic workup after epoxidation)
- Halogenation (due to the halonium intermediate): if this is carried out in the presence of water or ethers, halohydrin or haloether addition can occur.
- Oxymercuration-demurcuration (due to the mercurinium intermediate)
Most of these have in common a first step in which concerted syn addition occurs, following by an SN2 step where a nucleophile attacks the more electrophilic carbon (generally Markovnikov regioselectivity).