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23.15.2.1.5 Method 5: Bisketenes by Wolff Rearrangement of Bis(diazo ketones)

DOI: 10.1055/sos-SD-023-00632

Tidwell, T. T.Science of Synthesis, (200623706.

The Wolff rearrangement[‌36‌] is very useful for the generation of ketenes, and photolysis of bis(diazo ketones) 135 in ethanol completes a double ArndtEistert chain extension to form esters 137, in a process that can formally be represented as proceeding via bisketenes 136 (Scheme 47).[‌79‌] A similar reaction in which the spacer between the oxovinyl groups contained a 1,4-disubstituted phenyl ring gives a 70% yield of the diester.[‌80‌] The diesters prepared in these reactions are used for cyclization by acyloin reactions.[‌79‌,‌80‌]

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