1957
DOI: 10.1039/jr9570003755
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739. Hydrogenolysis of aromatic carbonyl compounds and alcohols with aluminium chloride and lithium aluminium hydride

Abstract: Brown and White. 3755 739. Hydrogenolysis of Aromatic Carbonyl Compounds and Alcohols with A luminiurn Chloride and Lithium A l u m i n i u m Hydride.

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Cited by 59 publications
(10 citation statements)
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“…3 well. Higher activities for 3' -chI oro (4), 3' -bromo (8), and 4'-dimethylamino (21) derivatives than were expected were also found.…”
Section: Structure-activity Relationshipsupporting
confidence: 62%
“…3 well. Higher activities for 3' -chI oro (4), 3' -bromo (8), and 4'-dimethylamino (21) derivatives than were expected were also found.…”
Section: Structure-activity Relationshipsupporting
confidence: 62%
“…The product, previously reported as A4-cholestene (13), was shown to be a mixture of cholestene with about 10% cholestane. Hydrogeilolysis has been observed in the reduction of other compounds by this reagent (14,15). Cholest-5-en-3-one gave a mixture which contained Can.…”
Section: Discussionmentioning
confidence: 99%
“…An aluminum chloride-lithium aluminum hydride (LAH) mixture (2:1) works well for the reduction of electron-rich benzopyranones but gives increasing amounts of 3,4-dehydrobenzopyrans upon ring deactivation. 12 The 3,4-dehydrobenzopyrans resulting from elimination rather than from reduction are difficult to separate from the desired products.13 Significant amounts of ether-cleavage products were obtained when the C-2 and C-8 positions are hydrogen-substituted. In cases where elimination and/ or ether cleavage was problematic, an alternative reduction method was employed.…”
Section: Synthetic Chemistrymentioning
confidence: 99%