Facile and Chemo-selective Cleavages of Allyl Ethers Utilizing Tetrabutylammonium Sulfate Radical Species

Abstract

Allyl ethers containing various functional groups reacted with tetrabutylammonium peroxydisulfate in acetonitrile under mild conditions to afford the corresponding cleaved alcohols in excellent yields.

Key words

cleavage of allyl ethers - tetrabutylammonium peroxydisulfate - chemo-selectivity - deprotection

References

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8

The allyl ether containing aldehyde moiety 2m reacted with DIBAL-H (1 equiv) in the presence of NiCl₂[dppp] in the short reaction time (30 min) resulted in the corresponding alcohols as shown below (Equation 5).

Equation 5

11

The aldehyde 4 was isolated (80%) and confirmed through GC analysis by comparison with the authentic sample of acrolein.