Diiodoindium(III) cation, InI₂⁺, a potent yneophile. Generation and application to cationic cyclization by selective
Karavadhi Surendra1, E J Corey
1Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
Abstract:
The removal of the iodide ion from indium triiodide by means of reactive Ag(I) salts leads to the formation of the highly reactive ligandless cation InI2(+), which is unusual in having two vacant low-lying p-orbitals. This bivalent Lewis acidity leads to an especially high affinity for the two orthogonal π-bonds of carbon-carbon triple bonds. Consequently, the double-coordinating InI2(+) is an especially effective reagent for the selective activation of C≡C and the catalytic initiation of cationic cyclization processes. A number of such reactions are described to demonstrate synthetic utility.
More Related Videos
10:14Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography
Published on: May 16, 2014
12:27Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cationic Chain-Growth Polymerization: Mechanism
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Pericyclic Reactions: Introduction
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
