ChemInform Abstract: Solvent Effects on the Rearrangements of Tertiary Alkynols.

✍ Scribed by X. HERAULT; E. MC NELIS

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199737067

✦ Synopsis

Solvent Effects on the Rearrangements of Tertiary Alkynols.

-Water effects remarkably iodonium-induced rearrangement of linear alkynols in acetonitrile: While in aqueous solutions β-iodo-. alpha.,β-unsaturated ketones, e.g. (II), (IV), and (VI), are the principal reaction products, in dry acetonitrile Iodo-Meyer-Schuster rearrangement leads to α-iodo-α,β-unsaturated aldehydes, e.g. (VII). The future synthetic value of this water effect, which affords separate preparation of shift or rearrangement products, lies in its extension to pharmacologically active cyclic alkynols. -(HERAULT, X.; MC NELIS, E.;