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Please login to access the full content or check if you have access via23.14.1.2.2 Method 2: Alkanoic Acid Derivatives by Addition of Heteroatom Nucleophiles to Monoalkylketenes
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DOI:
10.1055/sos-SD-023-00535
Tidwell, T. T., Science of Synthesis, (2006) 23, 592.
Monoalkylketenes react readily with alcohols, amines, or thiols to form esters, amides, and thioesters, respectively. This procedure is particularly useful in the capture of ketenes generated by the Wolff rearrangement, resulting in chain elongation by one carbon: this is known as the Arndt–Eistert reaction (see Section 23.14.1.2.2.1 and Section 23.14.1.2.2.2). The Kowalski reaction (see Section 23.14.1.2.2.3) accomplishes the same transformation, but by a completely different chemistry. Reactions with nucleophiles are often carried out to establish the intermediacy of a ketene in a particular reaction, or in other special circumstances.
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