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DOI: 10.1055/sos-SD-025-00010

Podlech, J.Science of Synthesis, (20072526.

The oxidation of primary alkyl halides 4 (X=Hal) or 4-toluenesulfonates 4 (X=OTs) to aldehydes 5 can also be achieved by treatment with trimethylamine N-oxide (Scheme 3). These reactions are performed in either chloroform[‌14‌] or dimethyl sulfoxide;[‌15‌,‌16‌] the latter solvent gives significantly better yields. Other amine oxides such as pyridine N-oxide are less suitable, and only a poor yield (38%) is obtained when this N-oxide is used to oxidize the bromide 4 (R1=OTHP; n=5; X=Br) to the substituted hexanal (5, R1=OTHP; n=5). A much better result is forthcoming when pyridine N-oxide is replaced by trimethylamine N-oxide; this gives the same hexanal (5, R1=OTHP; n=5) in 90% yield.[‌17‌]

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