Alcohols aldehydes prim

Bronsted acids form pyridinium salts (2 pK of pyridine 5.2) some of them are used as reagents in synthesis, for example, the chlorochromate (2, X = CrOsCl) and the dichromate (2, X = CriOy/l) as oxidants (prim, alcohol -> aldehyde sec. alcohol ketone) or the perbromide (2, X = Br3) as a brominating agent. 

Carbodiimide/dimethyl sulfoxide Oxo compounds from alcohols Aldehydes from prim, alcohols Selective oxidation... 

Hydrocarbon + 02 sec-Hydroperoxide prim-Hydroperoxide Alcohol + 0.5O2 Ketone Aldehyde Peracid + ketone Peracid + aldehyde... 

Hall, M., Hauer, B., Stuermer, R., Kroutil, W., and Faber, K. 2006. Asymmetric whole-cell bioreduction of an oc,P-unsaturated aldehyde (citral) competing prim-alcohol dehydrogenase and C-C lyase activities. Tetrahedron Asymm., 17, 3058-3062. 

NaBH4 is superior to LiAlH4 in selective reductions. In "water or methanol soln., it is an effective reagent for the conversion of aldehydes and ketones to the corresponding alcohols. Aoid chlorides are reduced to prim, alcohols in non-aq. media, but carboxylic acids, anhydrides, esters and nitriles are practically unaffected.—E Cinnamaldehyde —> cinnamyl alcohol. Y 97%.—n-Butyryl chloride —n-butanol Y 81%. (F. e. s. S. W. Chaikin, W. G-. Brown, Am. Soc. 71,122 (1949) s. a. H. Heusser et al., Helv. 33, 1093 (1950).)... 

Nitrogen oxides Aldehydes from prim, alcohols s. 1,160 CH2OH —CHO... 

Sulfurated sodium boron hydride Prim, alcohols from aldehydes... 

Chromium trioxide pyridine Aldehydes from prim, alcohols s. 16, 320 s. a. E. J. Corey and K. Achiwa, Tetrah. Let. 1969, 1837... 

Dimethylandrostane-6a,17/ -diol refluxed 2 hrs. in a dry suspension of excess Ag-carbonate-on-Celite in benzene 4,4-dimethyl-17-ketoandrostan-6a-ol. Y 87.5%. - Sterically hindered hydroxyl groups are not oxidized. F. e., also aldehydes from prim, alcohols, s. M. Fetizon and M. Golfier, C. r. 267 (C), 900 (1968) Chem. Commun. 1969, 1102. 

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