Synlett 2002(3): 0492-0494
DOI: 10.1055/s-2002-20475
LETTER
© Georg Thieme Verlag Stuttgart · New York

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

Seung Gak Yang, Min Young Park, Yong Hae Kim*
Center for Molecular Design and Synthesis, Department of Chemistry, Korea Advanced Institute of Science and Technology, Taejon, 305-701, Korea
Fax: +82(42)8695818; e-Mail: kimyh@mail.kaist.ac.kr;
Further Information

Publication History

Received 7 December 2001
Publication Date:
05 February 2007 (online)

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.

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.