Alternatives to α-diazo ketones for tandem cyclization–cycloaddition and carbenoid–alkyne metathesis strategies. Novel cyclic enol–ether formation via carbonyl ylide rearrangement reactions

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Abstract
Attempts to form carbonyl ylides from free carbenes derived from diazirines or diazo compounds lacking electron-withdrawing substituents resulted in azine formation or Wolff rearrangement, respectively, lodonium ylides proved to be a possible alternative to α-diazo compounds for metallocarbenoid generation, similar reactivity being observed for both systems. Studies into the rearrangement chemistry of carbonyl ylides provided a novel cyclic enol–ether synthesis via a 1,4-hydrogen shift process.