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ChemInform Abstract: Synthesis of Tetrahydrofurans by a Tandem Hydrogen Atom Abstraction/Radical Nucleophilic Displacement Sequence.

✍ Scribed by David Crich; Xianhai Huang; Martin Newcomb

Publisher: John Wiley and Sons
Year: 2010
Weight: 30 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199942114

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✦ Synopsis

Synthesis of Tetrahydrofurans by a Tandem Hydrogen Atom Abstraction/Radical Nucleophilic Displacement Sequence.

-Vicinal radical nucleophilic substitution of several phthalimide-protected phosphoryloxypentanols (I) and (VI) affords tetrahydrofuran derivatives in good yields. Diphenyl phosphate is the best leaving group compared to diethyl phosphate or acetate. Reaction of diethyl phosphate (Id) affords only moderate yield of the furan derivative accompanied with a phosphatoxyalkyl migration (IV) and a reduction product (V); acetates like (Ic) do not undergo cyclization. As is shown for derivative (VII), the reaction sequence proceeds without diastereoselectivity. The reaction mechanism is discussed. -(CRICH,

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