What is it about?
Non-sensitized photochemical fluoroalkylation of alkanols provides exclusively monoalkylated products, Kharash-type major adducts (III) and anti-Kharash regioisomers (IV). Radical fluoroalkylations of butane-1,4-diol affords mono- (cf. (VI),(IX)) and bisalkylated products in low preparative yields (cf. (VII),(X)) under both photochemical and peroxide-initiated reactions. Surprisingly, photo- initiated nucleophilic addition of butanediol to perfluoropropene occurs in acetonitrile solutions containing Na2CO3 (! (XI),(XII) ). 1,2- as well as 1,3-diols are completely unreactive under radical fluoroalkylation conditions.
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Why is it important?
Non-sensitized photochemical fluoroalkylation of alkanols provides exclusively monoalkylated products, Kharash-type major adducts (III) and anti-Kharash regioisomers (IV). Radical fluoroalkylations of butane-1,4-diol affords mono- (cf. (VI),(IX)) and bisalkylated products in low preparative yields (cf. (VII),(X)) under both photochemical and peroxide-initiated reactions. Surprisingly, photo- initiated nucleophilic addition of butanediol to perfluoropropene occurs in acetonitrile solutions containing Na2CO3 (! (XI),(XII) ). 1,2- as well as 1,3-diols are completely unreactive under radical fluoroalkylation conditions.
Perspectives
Non-sensitized photochemical fluoroalkylation of alkanols provides exclusively monoalkylated products, Kharash-type major adducts (III) and anti-Kharash regioisomers (IV). Radical fluoroalkylations of butane-1,4-diol affords mono- (cf. (VI),(IX)) and bisalkylated products in low preparative yields (cf. (VII),(X)) under both photochemical and peroxide-initiated reactions. Surprisingly, photo- initiated nucleophilic addition of butanediol to perfluoropropene occurs in acetonitrile solutions containing Na2CO3 (! (XI),(XII) ). 1,2- as well as 1,3-diols are completely unreactive under radical fluoroalkylation conditions.
Dr Vladimír Církva
Institute of Chemical Process Fundamentals
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This page is a summary of: ChemInform Abstract: Radical Additions to Fluoroolefins. Photochemical Fluoroalkylation of Alkanols and Alkanediols with Perfluorovinyl Ethers; Photo‐Supported O‐ Alkylation of Butane‐1,4‐diol with Hexafluoropropene., ChemInform, April 1997, Wiley,
DOI: 10.1002/chin.199716091.
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