Editing Hydroboration–oxidation reaction (section)

==Alternative oxidations==
Use of other oxidants instead of hydrogen peroxide can lead to carbonyl products rather than alcohols from alkenes. [[N-Methylmorpholine N-oxide|''N''-Methylmorpholine ''N''-oxide]] with catalytic [[tetrapropylammonium perruthenate]] converts the alkylborane into a carbonyl, thus a ketone or [[aldehyde]] product depending on what other groups were attached to that carbon in the original alkene.<ref>{{cite journal |title= One-pot conversion of olefins to carbonyl compounds by hydroboration / NMO–TPAP oxidation |first1= Matthew H. |last1= Yates |journal= Tetrahedron Lett. |volume= 38 |pages= 2813–2816 |year= 1997 |doi= 10.1016/S0040-4039(97)00476-0 }}</ref> Various [[dichromate]]s or related [[chromium]](VI) reagents give ketones as well, but give [[carboxylic acid]]s instead of aldehydes for terminal alkenes.<ref>{{cite journal |title= Organoboranes for Synthesis. 14. Convenient Procedures for the Direct Oxidation of Organoboranes from Terminal Alkenes to Carboxylic Acids |first1= Herbert C. |last1= Brown |first2= Shekhar V. |last2= Kulkarni |first3= Vijay V. |last3= Khanna |first4= Virendra D. |last4= Patil |first5= Uday S. |last5= Racherla |journal= Journal of Organic Chemistry |year= 1992 |volume= 57 |issue= 23 |pages= 6173–6177 |doi= 10.1021/jo00049a024 }}</ref>