Lead Tetraacetate Induced Addition Reaction of Difluorodiiodomethane to Alkenes and Alkynes. Synthesis of Fluorinated Telechelic Compounds
- 31 December 1997
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1997 (12) , 1481-1488
- https://doi.org/10.1055/s-1997-1378
Abstract
Lead tetraacetate (LTA) can smoothly induce the addition reaction of difluorodiiodomethane (1) with electron-rich alkenes at 60°C in diglyme to give monoadducts (RCHICH2CF2I) and diadducts (RCHICH2)2. The similar, clean reaction of fluoroolefins, such as tetrafluoroethene, hexafluoropropene, with 1 occurs only in acetic acid. However, non-fluorinated β-iodo-α,β-unsaturated carboxylic esters are obtained when 1 reacts with alkynes in alcohol. The iododifluoromethyl radical generated by possible pathways from 1 with LTA is discussed.Keywords
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