Science of Synthesis

Podlech, J., Science of Synthesis, (2007) 25, 26.

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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References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) M 8, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.
• 8.Meeeee-Meee, (8888) M 8e8, 888.