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27.15.2.4.1 Beckmann Rearrangement

DOI: 10.1055/sos-SD-127-00117

Chiba, S.; Narasaka, K.Science of Synthesis Knowledge Updates, (20114475.

Conversion of oximes and O-substituted derivatives into amides (e.g., 52) and lactams is known as the Beckmann rearrangement (Scheme 42).[‌39‌,‌273‌,‌435‌,‌436‌] In general, the Beckmann rearrangement requires the use of excess amounts of acid such as sulfonic acid, hydrochloric acid, polyphosphoric acid,[‌437‌] or various Lewis acids. Among the variety of reagents available for this transformation are phosphorus pentachloride,[‌438‌] triphenylphosphine/carbon tetrachloride,[‌439‌] sulfuric acid,[‌440‌,‌441‌] thionyl chloride,[‌442‌] 4-toluenesulfonyl chloride/pyridine,[‌341‌,‌443‌] and phosphorus pentoxide/methanesulfonic acid.[‌444‌,‌445‌] Microwave irradiation[‌446‌] and photoirradiation[‌447‌,‌448‌] have also been reported.

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Meeeee 88 Meeeeeeee ee eee Meeeeeee Meeeeeeeeeeee[‌88‌]

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Meeeee 88 Meeeeeeeeeeeeeeeee Meeeeee Meeeeeee Meeeeeee Meeeeeeeeeeee ee ee Meeee[‌888‌]

Meee eeeee ee eeeeee eeeeeeeee eee ee eeeeeeee ee Meeeeeee eeeeeeeeeeeee ee eeeeee eeee ee eeeeeeeeeeeeee eeeeeeeeeeee eeeeee. Mee eeeee eee eeeeeeee: eeee eee eeeeeeeeeee ee eeeeeee ee eee eeee-eeeeeeeeeee ee eee eeeee M-eeeee eeeee, eee eeeeeeeeeee eeeeeeee ee eeee-eeee, eee eeeeeeeeeeeeee 88 ee eeeeeeee, eeeee ee eee eeeee eeee, e eeeeeeeeeeeeeee(eeeee)eeeee 88 ee eeeeee ee eee-eeee eeeeeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeeeeeeee eee Meeeeeeeeee ee Meeeee[‌88‌]

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M-Meeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌888‌]

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8,8,8,8-Meeeeeeeee-8,8-eeeeeeeeeeeeeee (88):[‌888‌]

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References