Russian Chemical Bulletin p. 2375 - 2381 (1995)
Update date:2022-07-29
Topics:
Kartashov, V. R.
Sokolova, T. N.
Pavinskii, I. V.
Timofeev, I. V
Radbil', A. V.
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.
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