Lead Tetraacetate Induced Addition Reaction of Difluorodiiodomethane to Alkenes and Alkynes. Synthesis of Fluorinated Telechelic Compounds

An-Rong Li; Qing-Yun Chen

doi:10.1055/s-1997-1378

Synthesis 1997; 1997(12): 1481-1488
DOI: 10.1055/s-1997-1378

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Lead Tetraacetate Induced Addition Reaction of Difluorodiiodomethane to Alkenes and Alkynes. Synthesis of Fluorinated Telechelic Compounds

An-Rong Li, Qing-Yun Chen^*

^*Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Fenglin Lu, Shanghai, 200032, China, Fax +86(21)64166128; E-mail: chenqy@pub.sioc.ac.cn

Abstract

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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.

difluorodiiodomethane - lead tetraacetate - alkene - alkyne - addition

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