In:
Canadian Journal of Chemistry, Canadian Science Publishing, Vol. 68, No. 5 ( 1990-05-01), p. 720-724
Abstract:
The less reactive carbonyl group of a mixture of reducible groups of carbonyl compounds was preferentially reduced with diborane on silica gel by first forming an adduct of the more reactive carbonyl group with sodium bisulfite. For example, 4-acetylbenzaldehyde could be converted to 4-(1-hydroxylethyl)benzaldehyde in 93% selectivity; in a mixture of 4-phenyl-acetophenone and 4-phenylbenzaldehyde, biphenylethanol was preferentially formed in 95% yield with 16% yield of 4-phenylbenzyl alcohol. Silica gel and sodium bisulfite were essential for this selective reaction. Aliphatic and aromatic aldehydes and unhindered cyclohexanones could be selectively protected by this method. Keywords: sodium bisulfite, silica gel, carbonyl compound, selective reduction, diborane.
Type of Medium:
Online Resource
ISSN:
0008-4042
,
1480-3291
Language:
English
Publisher:
Canadian Science Publishing
Publication Date:
1990
detail.hit.zdb_id:
1482256-8
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