The unstabilised Wittig reaction selectively forms cis alkenes

the verdict

SUPPORTED

the evidence backs this

Recorded sources

3 sources for · 0 against

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The unstabilised Wittig reaction is well-known in organic chemistry for its selectivity in yielding cis (Z) alkenes via kinetic control.

The analysis

The retrieved papers (specifically [1], [4], and [8]) discuss the mechanism and stereochemical outcome of Wittig reactions, confirming that non-stabilized (unstabilized) phosphonium ylides selectively form cis-oxaphosphetanes and subsequently cis alkenes under kinetic control.

Evidence for · 3

The modern interpretation of the Wittig reaction mechanism.

Recorded source metadata

Peter A. Byrne, D. Gilheany. The modern interpretation of the Wittig reaction mechanism.. 2013. https://doi.org/10.1039/c3cs60105f

Reviews the mechanism of Wittig reactions and confirms that non-stabilized ylides operate under kinetic control to yield specific stereochemical outcomes.

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More for · 2

Unequivocal experimental evidence for a unified lithium salt-free Wittig reaction mechanism for all phosphonium Ylide types: reactions with β-heteroatom-substituted aldehydes are consistently selective for cis-oxaphosphetane-derived products.

Recorded source metadata

Peter A. Byrne, D. Gilheany. Unequivocal experimental evidence for a unified lithium salt-free Wittig reaction mechanism for all phosphonium Ylide types: reactions with β-heteroatom-substituted aldehydes are consistently selective for cis-oxaphosphetane-derived products.. 2012. https://doi.org/10.1021/ja300943z

Demonstrates that Wittig reactions involving non-stabilized ylides consistently produce cis-oxaphosphetane-derived products under salt-free conditions.

Source citation format

Dissection of the mechanism of the Wittig reaction.

Recorded source metadata

Paola Farfán, S. Gómez, Albeiro Restrepo. Dissection of the mechanism of the Wittig reaction.. 2019. https://doi.org/10.1021/acs.joc.9b02224

Details how the transition state of the salt-free Wittig reaction connects the initial C-C bond formation to the stereochemistry of the resulting alkene.

Source citation format

The paper trail · every fact has a biography

first checked01 Aug 2026

judged → SUPPORTED · 9001 Aug 2026

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