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37.2.3.2 Method 2: Addition of a Bismuthonium Ylide

DOI: 10.1055/sos-SD-037-00188

Aggarwal, V. K.; Crimmin, M.; Riches, S.Science of Synthesis, (200837328.

Bismuthonium ylides are significantly less stabilized than their sulfonium analogues and are not commonly applied in organic synthesis. Their comparative instability provides a degree of complementarity for these ylides because ketone-stabilized sulfonium ylides do not tend to undergo carbonyl epoxidation whereas the bismuthonium analogues do. Also, highly stabilized sulfonium ylides tend to undergo 1,4-addition to α,β-unsaturated aldehydes to give the cyclopropanes as a consequence of highly reversible 1,2-addition {see Science of Synthesis, Vol. 27 [Heteroatom Analogues of Aldehydes and Ketones (Section 27.1.3.2.427.1.3.2.4)]}, whereas bismuthonium ylides bearing similar substituents undergo 1,2-addition to give epoxides.

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