Whiting reaction

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title: "Whiting reaction" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["organic-redox-reactions", "name-reactions"] description: "Chemical reaction" topic_path: "general/organic-redox-reactions" source: "https://en.wikipedia.org/wiki/Whiting_reaction" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical reaction ::

The Whiting reaction is an organic reaction converting a propargyl diol into a diene using lithium aluminium hydride.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/3/36/WhitingReactionGeneral.png" caption="Whiting reaction"] ::

This organic reduction has been applied in the synthesis of fecapentaene, a suspected cause of colon cancer: :[[Image:WhitingReaction.png|center|500px|alt=SMILES-esque: thp is CC1CCCCO1, tbdms is CSi(C)(C)C(C)(C)C. Step 1 is CCC=CC=CC(Othp)C#CC(O)C=COCC(Otbdms)COtbdms, to which is added LiAlH4 in THF to obtain Step 2, namely CCC=CC=CC=CC=CC=COCC(Otbdms)COtbdms, to which is added nBu4NF in THF/Et2O to obtain Step 3, namely CCC=CC=CC=CC=CC=COCC(O)CO]] Protecting groups are tetrahydropyranyl and TBSMS; the final step is deprotection with tetra-n-butylammonium fluoride.

References

References

1. Nayler, P.; Whiting, M. C. ''[[J. Chem. Soc.]]'' '''1954''', 4006–09.
2. ''Synthesis of crystalline (.+-.)-fecapentaene'' Hans Rudolf Pfaendler, Franz Karl Maier, and Sonja Klar [[J. Am. Chem. Soc.]]; '''1986'''; 108(6) pp. 1338–39. ({{doi. 10.1021/ja00266a057)

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