Whiting reaction

{{Short description|Chemical reaction}}

{{Use dmy dates|date=March 2024}}

The Whiting reaction is an organic reaction converting a propargyl diol into a diene using lithium aluminium hydride.Nayler, P.; Whiting, M. C. J. Chem. Soc. 1954, 4006–09.

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This organic reduction has been applied in the synthesis of fecapentaene, a suspected cause of colon cancer: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}})

:Image:WhitingReaction.png

Protecting groups are tetrahydropyranyl and TBSMS; the final step is deprotection with tetra-n-butylammonium fluoride.