KINETICS AND MECHANISM OF AZIDOMERCURATION OF ALKENES, CYCLOALKENES, AND THEIR DERIVATIVES WITH A MERCURIC ACETATE-SODIUM AZIDE SYSTEM

Authors
KARTASHOV VR SOKOLOVA TN PAVINSKII AY TIMOFEEV IV RADBIL AB
Citation
Vr. Kartashov et al., KINETICS AND MECHANISM OF AZIDOMERCURATION OF ALKENES, CYCLOALKENES, AND THEIR DERIVATIVES WITH A MERCURIC ACETATE-SODIUM AZIDE SYSTEM, Russian chemical bulletin, 44(12), 1995, pp. 2375-2381
Citations number
21
Categorie Soggetti
Chemistry
Journal title
Russian chemical bulletin → ACNP
ISSN journal
10665285
Volume
44
Issue
12
Year of publication
1995
Pages
2375 - 2381
Database
ISI
SICI code
1066-5285(1995)44:12<2375:KAMOAO>2.0.ZU;2-Q
Abstract
The kinetics of azidomercuration of alkenes, cycloalkenes, and their d erivatives 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 resul ts, it was concluded that HgOAcN3 and Hg(N-3)(2) play the role of azid omercuration reagents. The reactions with alkenes having a strained do uble bond occur by a concerted scheme. With nonstrained alkenes, a mul tistep mechanism is realized, its first reversible step involving the formation of a mercurinium intermediate with an ion pair structure.