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23.3.3.2.6 Method 6: Mixed Dimerization of Bromo(tert-butyl)ketenes with tert-Butylketene

DOI: 10.1055/sos-SD-023-00080

Tidwell, T. T.Science of Synthesis, (200623163.

Addition of triethylamine to a refluxing mixture of 1 equivalent of 2-bromo-3,3-dimethyl­acetyl chloride (280) and 1 equivalent of tert-butylacetyl chloride (281) in benzene leads to the dimer 284 formed by a [2+2]-mixed cyclodimerization of the two ketenes 282 and 283 (Scheme 103).[‌185‌] The structure of the dimer can be established by methanolysis to the oxo ester 285, which indicates that nucleophilic attack occurs on the less crowded tert-butylketene (283).[‌185‌]

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