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Anchimerically assisted lewis acid cleavage of tetrahydrofurans to furnish 1,4-Diols

✍ Scribed by Laurence M. Harwood; Brian Jackson; Keith Prout; Fiona J. Witt

Book ID: 104228963
Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 176 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)98811-7

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✦ Synopsis

Treatment of 3-aroyloxy-and 2-(aroyloxymethyl)tetrahydrofurans with TiCI 4 results in cleavage of the heterocyclic ring with intervention by the appropriately situated ester group to form intermediates which, on work-up and hydrolysis, furnish 1,4-diols.

The Lewis acid mediated cleavage of tetrahydrofurans to furnish appropriately 1,4-functionalised acyclic materials is a highly useful conversion having many variants) However, the majority of procedures result in the introduction of the Lewis acid counterion and, with some notable exceptions, 2 show little regiochemical differentiation with unsymmetrically substituted substrates (Figure 1).

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