Kinetics and mechanism of azidomercuration of alkenes, cycloalkenes, and their derivatives with a mercuric acetate-sodium azide system

Article abstract of DOI:10.1007/BF00713611

The kinetics of azidomercuration of alkenes, cycloalkenes, and their derivatives with a Hg(OAc)2-NaN3 system (1:1, 1:2, and 1:3) was studied.Based on the data on the product structure and kinetic results, it was concluded that HgOAcN3 and Hg(N3)2 play the role of azidomercuration reagents.The reaction with alkenes having a strained double bond occur by a concerted scheme.With nonstrained alkenes, a multistep mechanism is realized, in the first reversible step involving the formation of a mercurinium intermediate with an ion pair structure. - Key words: azidomercuration, alkenes, cycloalkenes, strained double bond, kinetics, reaction mechanism.