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Salaün, J., Science of Synthesis, (2005) 26, 564.
Commercially available cyclopropylmethanol (see also Section 26.2.1.11) undergoes acid-induced ring expansion by aqueous hydrochloric acid at 100°C to furnish cyclobutanol in 57% yield (Scheme 13).[29] Cyclobutanol is oxidized by chromium(VI) oxide and oxalic acid to provide cyclobutanone (3) in 31–35% yield from cyclopropylmethanol (Scheme 13).[30] Alternatively, oxidation of cyclobutanol into cyclobutanone (3) occurs with chromic acid–pyridine complex in pyridine, but no yield was reported.[31] 1-Hydroxycyclobutanecarboxylic acid[32,33] also undergoes thermal decarboxylation to provide cyclobutanone (3) in 15% yield.[32]
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References
| [29] | Meeeüe, M.; Meeee, M., Mee. Meeee., Meee. Mee. MMM, (8888), 888. |
| [30] | Meeeeeee, M.; Meeee, M., Mee. Meeee., Meee. Mee. MMM, (8888), 888. |
| [31] | Meeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 888. |
| [32] | Meeeeeee, M. M.; Meeeeeeee, M., Meee. Mee., (8888) 88, 8888. |
| [33] | Meeeee, M.; Meeeeeee, M.; Meeeüe, M., Meeeeeeeeee, (8888) 88, 8888. |
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- 8.Meeeee-Meee, (8888) M 88e, 888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
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