The Number of Hydride Ions in AlH2Cl Available for Hydrogenolysis of 1,3-Dioxolanes
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2-Methyl-1,3-dioxolane (1) in ether is hydrogenolyzed completely to 2-ethoxyethanol by an equimolar proportion of AlH2Cl, whereas a 1/2 mol of AlH2Cl hydrogenolyzes 1 mol of 1 only to the extent of 50%. In the latter case, the intermediate compound 2-ethoxyethoxyhydridoaluminum chloride (C2H5OCH2CH2OAlHCl) formed with half of the 2-methyl-1,3-dioxolane, even though it contains a hydride ion, fails to react with the remainder of the dioxolane. This is believed due to the preference of C2H5OCH2CH2OAlHCl to form an internal Lewis acid-base complex rather than form a similar complex with 1, a step essential to facilitate the hydrogenolysis of 1.
2021 ◽
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2007 ◽
Vol 111
(6)
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pp. 1402-1407
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2001 ◽
Vol 81
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pp. 908-917
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2013 ◽
Vol 19
(11)
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pp. 4805-4813
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2003 ◽
Vol 6
(6)
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pp. A113
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