Tetrahedron

Organoboranes for synthesis. 4: Oxidation of organoboranes with pyridinium chlorochromate. A direct synthesis of aldehydes from terminal alkenes via hydroboration

HC Brown, SU Kulkarni, CG Rao, VD Patil

Index: Brown, Herbert C.; Kulkarni, Surendra U.; Rao, C. Gundu; Patil, Vemanna D. Tetrahedron, 1986 , vol. 42, # 20 p. 5515 - 5522

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Citation Number: 36

Abstract

The oxidation of trialkylboranes containing primary a1kyl groups with pyridinium chlorochromate (PCC) in methylene chloride provides the corresponding aldehydes in good yields. The stoichiometry for the oxidation of alcohols, borate esters and trialkylboranes with PCC has been examined. In view of the poor regioselectivity (only 94% primary alkyl groups) and functional group tolerance observed in the hydroboration with borane (BH3. ...