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23.14.1.2.2.1 Variation 1: Alkanoic Acid Derivatives by the Arndt–Eistert Chain Elongation

DOI: 10.1055/sos-SD-023-00535

Tidwell, T. T.Science of Synthesis, (200623592.

The ArndtEistert reaction involves Wolff rearrangement in the presence of nucleophilic solvents to form ketenes that are captured by the solvent, and it provides a method for chain elongation of carboxylic acids by one carbon;[‌100‌] further information on this reaction can be found in HoubenWeyl, Vol. 10/4, p 473. The preparation of equilenin, an early landmark in total synthesis, involves the Wolff rearrangement of the diazo ketone 134 to give the ketene 135 that is captured by methanol to form the intermediate 136, which is used in the synthesis of equilenin (Scheme 42).[‌101‌]

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