129461-30-9Relevant academic research and scientific papers
SELECTIVE PROTECTION OF CARBONYL COMPOUNDS BY GIRARD'S REAGENT USING SILICA GEL AS A SOLID SUPPORT
Chihara, Teiji,Waniguchi, Erika,Wakabayashi, Tamie,Taya, Kazuo
, p. 1647 - 1648 (1983)
The Girard's reagent, which gives water-soluble derivatives of carbonyl compounds, was used together with silica gel as a protective reagent of them in a non-aqueous solvent system.Less hindered or more reactive carbonyl compounds were selectively protected by this method in competitive reductions.
Selective reduction of less reactive carbonyl groups in the presence of diborane and sodium bisulfite on silica gel
Chihara, Teiji,Wakabayasi, Tamie,Taya, Kazuo,Ogawa, Haruo
, p. 720 - 724 (2007/10/02)
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 the adduct of the more reactive carbonyl group with sodium bisulfite.For example, 4-acetylbenzaldehyde could be converted to 4-(1-hydroxylethyl)benzaldehyde in 93percent selectivity; in a mixture of 4-phenyl-acetophenone and 4-phenylbenzaldehyde, biphenylethanol was preferentially formed in 95percent yield with 16percent 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.
