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Oxidative rearrangement can also go through an allylic cation generated by solvolysis of the chromate ester, as similarly described in Scheme 4 (vide infra). See also ref 4.
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We reasoned that the carboxy group imparts considerable solubility in DMSO and suitable acidity to IBX.
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85039469207
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4 and concentrated in vacuo. The remaining residue was purified by column chromatography on silica gel to give 85% of 1b.
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33
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85039463452
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note
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(16) Addition of pyridine had unpredictable results. For example, it suppressed the dehydration of 1a and decreased the yield of 1b to 70% due to the contamination of dark-brown byproducts derived from pyridine.
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