Year: 2014
Type: review
Abstract: The review deals with the literature dealing with the use of reagents 1-(trifluoromethyl)-1,2-benziodoxol-3(1H)-one (1) and trifluoromethyl-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (2) and is subdivided into four main sections describing synthesis, structure and properties activation and application. The crystalline nature of these compounds allowed the structural features of 1 and 2 to be analyzed by X-ray crystallography.These analyses show a typical distorted T-shape geometry around iodine arising from a pseudotrigonal bipyramidal geometry where the two lone pairs at iodine occupy equatorial positions. Cyclic voltammetry studies have been performed on both 1 and 2. Depending on the exact experimental conditions, values of the one-electron reduction potential ranging between -1.10 and -0.94 V versus standard calomel electrode (SCE) have been determined for 1, while the values for 2 are found to be between -1.82 and -1.09 V. Trifluoromethylation of acetylenes was explored in the early days of reagents 1 and 2 .Instead of the desired trifluoromethylated acetylene, trifluoromethyl triflate (TFMT) was formed from the reaction of reagent 1 and the anion of the zinc salt.
Source: Chemical Reviews
DOI: 10.1021/cr500223h
Authors: Julie Charpentier, Natalja Früh, Antonio Togni
Institution: ETH Zurich
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
OpenAlex ID: W2009008810