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43.8.2.1.6.3 Variation 3: Alkynes by [2,3]-Sigmatropic Rearrangement

DOI: 10.1055/sos-SD-043-00415

Krueger, A.Science of Synthesis, (200843495.

There are also a few examples of [2,3]-sigmatropic rearrangements leading to alkynes.[‌118‌,‌119‌] Allenic sulfur compounds such as 76 are transformed into the respective sulfur ylides 77 by reaction with diazomethane. The subsequent [2,3]-sigmatropic rearrangement yields the respective alkynes 78 (Scheme 35).[‌118‌]

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M8 Meeeeeeeee Meeeee (%) Mee
M MM8M8 (8 eeeee), MeMe, 88°M, 8e 88 (88) [‌888‌]
Me MM8M8 (8 eeeee), MeMe, 88°M, 8e 88 (88) [‌888‌]

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