Vanadium(III) Chloride (VCl3): Efficient Reagent for the Introduction of Tetrahydrofuran‐Based Acetal Protecting Groups for Alcohols |
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| Authors: | Biswanath Das Maddeboina Krishnaiah Vtukuri Saidi Reddy Keetha Laxminarayana |
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| Affiliation: | 1. Organic Chemistry Division‐I, Indian Institute of Chemical Technology, Hyderabad‐500?007, India, (phone: +91‐40‐7193434;2. fax: +91‐40‐7160512) |
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| Abstract: | Treatment of different types of alcohols with tetrahydrofuran (THF) in the presence of VCl3 and CCl4 smoothly afforded the corresponding THF‐based acetals in excellent yields. The reaction is fast at room temperature, and several functional groups are tolerated, with no racemization being observed. A radical mechanism, based on Cl3C. as the active species, is proposed for this novel kind of transformation, which complements the classical tetrahydro‐2H‐pyran‐2‐yl (THP) protocol. |
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| Keywords: | Vanadium(III) chloride Protecting groups Tetrahydrofuran (THF) Carbon tetrachloride Radical mechanism Alcohols |
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