Onium transfer reaction of (beta,beta-dialkylvinyl)(phenyl)iodonium tetrafluoroborates via an alkylidene carbene pathway: Synthesis of group 15 alkenyl(triphenyl)- and group 16 alkenyl(diphenyl)onium salts

Authors
Ochiai, M Sueda, T Noda, R Shiro, M
Citation
M. Ochiai et al., Onium transfer reaction of (beta,beta-dialkylvinyl)(phenyl)iodonium tetrafluoroborates via an alkylidene carbene pathway: Synthesis of group 15 alkenyl(triphenyl)- and group 16 alkenyl(diphenyl)onium salts, J ORG CHEM, 64(23), 1999, pp. 8563-8567
Citations number
55
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
23
Year of publication
1999
Pages
8563 - 8567
Database
ISI
SICI code
0022-3263(19991112)64:23<8563:OTRO(T>2.0.ZU;2-D
Abstract
Group 15 1-alkenyl(triphenyl)onium (P, As, Sb) tetrafluoroborates were prep ared via an onium transfer reaction of alkenyl(phenyl)iodonium tetrafluorob orates under mild conditions. The reaction involves base-induced reductive alpha-elimination of the iodonium salts, followed by nucleophilic trapping of the resulting free alkylidene carbenes with group 15 element-centered nu cleophiles. The onium transfer reaction of the alkenyliodonium salts also p roduced group 16 1-alkenyl(diphenyl)onium (S, Se, Te) tetrafluoroborates in good yields.