RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2002(3): 0492-0494
DOI: 10.1055/s-2002-20475
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
Weitere Informationen
Received
7 December 2001
Publikationsdatum:
05. Februar 2007 (online)
Publikationsverlauf
Publikationsdatum:
05. Februar 2007 (online)
![](https://www.thieme-connect.de/media/synlett/200203/lookinside/thumbnails/10.1055-s-2002-20475-1.jpg)
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
- 1
Cunninghan J.Gigg R.Warren CD. Tetrahedron Lett. 1964, 1191 - 2
Guibe F. Tetrahedron 1997, 53: 13509 - For pertinent monographs, see:
-
3a
Greene TW.Wuts PGM. Protective Groups in Organic Synthesis 2nd ed.: Wiley; New York: 1991. -
3b
Kocienski PJ. Protecting Groups Thieme; Stuttgart: 1994. -
4a
Gent PA.Grigg R. J. Chem. Soc., Chem. Commun. 1974, 277 -
4b
Grigg R. J. Chem. Soc., Perkin Trans. 1 1980, 738 - 5
Grigg J.Grigg R. J. Chem. Soc., Chem. Commun. 1966, 82 -
6a
Espanet B.Bunach E.Perichon Y. Tetrahedron Lett. 1992, 33: 2485 -
6b
Kadam SM.Nayak SK.Banerji A. Tetrahedron Lett. 1992, 33: 5129 -
6c
Mereyala HB.Guntha S. Tetrahedron Lett. 1993, 34: 6929 -
6d
Ito H.Taguchi T.Hazawa Y. J. Org. Chem. 1993, 58: 774 -
6e
Diaz RR.Melagatejo CR.Lopez-Espinosa MTP.Cubero II. J. Org. Chem. 1994, 59: 7928 -
6f
Lee J.Cha JK. Tetrahedron Lett. 1996, 37: 3663 -
6g
Honda M.Morita H.Nagaku I. J. Org. Chem. 1997, 62: 8932 -
6h
Yu B.Li B.Zhang J.Hui Y. Tetrahedron Lett. 1998, 39: 4871 - 7
Taniguchi T.Ogasawara K. Angew. Chem. Int. Ed. 1998, 37: 1136 - 9
Yadav JS.Chardrasekhar S.Sumitra G.Kacke R. Tetrahedron Lett. 1996, 37: 6603 -
10a
Jung JC.Choi HC.Kim YH. Tetrahedron Lett. 1993, 34: 3581 -
10b
Choi HC.Kim YH. Synth. Commun. 1994, 24: 2307 -
10c
Choi HC.Cho KI.Kim YH. Synlett 1995, 207 -
10d
Yang SG.Lee DH.Kim YH. Heteroat. Chem. 1997, 8: 435 -
10e
Hwang JP.Yang SG.Kim YH. Chem. Commun. 1997, 1355 -
10f
Kim YH.Hwang JP.Yang SG. Tetrahedron Lett. 1997, 38: 3009
References
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
The aldehyde 4 was isolated (80%) and confirmed through GC analysis by comparison with the authentic sample of acrolein.