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You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content. Variation 2: Homologation by Multiple Carbon Atoms

DOI: 10.1055/sos-SD-020-00203

Vedantham, P.; Jiménez, M.; Hanson, P. R.Science of Synthesis, (200720279.

Carboxylic acids can be homologated by more than one carbon using metal-catalyzed processes. In general the homologation products may be formed by reaction of a carboxylic acid with an allene, catalyzed by either a rhodium or copper species. For example, allene reacts with but-3-enoic acid at 85°C, using catalytic amounts of chlorotris(triphenylphosphine)rhodium(I), and two possible products are formed in 23% yield. These are a 3,5-dienoic acid 48 and a 3,6-dienoic acid 49, and this mixture is attributed to the ability of the allene to form either an allylic or vinylic system with the metal (Scheme 19).[‌39‌]

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M8 Meeee (88/88) Meeee (%) Mee
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Mee-8-eeeee Meee (88, e=8); Meeeeee Meeeeeeee:[‌88‌]

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Meeeeee-88,88-eeeeeee Meee (88, e=88; e=8); Meeeeee Meeeeeeee:[‌88‌]

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Meeeeeeeee Meee 88; Meeeeee Meeeeeeee:[‌88‌]

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