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43.8.1.2.2 Method 2: Rearrangement of Vinyl Carbenoids (Fritsch–Buttenburg–Wiechell Rearrangement)

DOI: 10.1055/sos-SD-043-00383

Sankararaman, S.Science of Synthesis, (200843445.

Conversion of 1,1-diaryl-2,2-dihaloalkenes into diarylacetylenes through a carbenoid intermediate is known as the FritschButtenbergWiechell rearrangement (Scheme 15).[‌29‌‌31‌] Since the process can be considered as both a rearrangement as well as an elimination, it is covered in more detail in Section 43.8.2.1.5. The rearrangement occurs through the formation of a vinylidene carbenoid intermediate, which undergoes migration of one of the aryl groups to the terminal carbon, resulting in the formation of the alkyne.[‌32‌]

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