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-00000084.xml
Synthesis 2011(13): 2125-2130
DOI: 10.1055/s-0030-1260605
DOI: 10.1055/s-0030-1260605
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Terpenic Compounds as Renewable Sources of Raw Materials for Cross-Metathesis
Weitere Informationen
Received
22 March 2011
Publikationsdatum:
26. Mai 2011 (online)
Publikationsverlauf
Publikationsdatum:
26. Mai 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201113/lookinside/thumbnails/10.1055-s-0030-1260605-1.jpg)
Abstract
Dihydromyrcenol is used as a hydrated masked form of citronellene in olefin cross-metathesis reactions in order to solve the selectivity problem that results from the presence of two double bonds in many terpenes. Several ruthenium catalysts are evaluated, with the best, M71-SIPr, utilized in the cross-metathesis of dihydromyrcenol with various olefins affording the expected products in good yields. It is shown that the masked double bond can be regenerated via an acid-catalyzed elimination reaction and the product is then subjected to a further cross-metathesis reaction with a second olefin.
Key words
terpenoids - olefin metathesis - chemoselectivity - agro-resources - dihydromyrcenol
-
1a
Monomers, Polymers and Composites from Renewable Resources
Belgacem MN.Gandini A. Elsevier; Amsterdam: 2008. -
1b
Corma A.Iborra S.Velty A. Chem. Rev. 2007, 107: 2411 -
2a
Malacea R.Fischmeister C.Bruneau C.Dubois J.-L.Couturier J.-L.Dixneuf PH. Green. Chem. 2009, 11: 152 -
2b
Le Ravalec V.Fischmeister C.Bruneau C. Adv. Synth. Catal. 2009, 351: 1115 -
2c
Borre E.Pieck CA.Caijo F.Crévisy C.Mauduit M. Chem. Today 2009, 27: 74 -
2d
Behr A.Westfechtel A.Gomes JP. Chem. Eng. Technol. 2008, 31: 700 -
2e
Rybak A.Meier MAR. Green Chem. 2007, 9: 1356 -
2f
Burdett KA.Harris LD.Margl P.Maughon BR.Mokhtar-Zadeh T.Saucier PC.Wasserman EP. Organometallics 2004, 23: 2027 -
2g
Dinger MB.Mol JC. Adv. Synth. Catal. 2002, 344: 671 ; and references cited therein -
3a
Meylemans HA.Quintana RL.Goldsmith BR.Harvey BG. ChemSusChem 2011, 4: 465 -
3b
Vieille-Petit L.Clavier H.Linden A.Blumentritt S.Nolan SP.Dorta R. Organometallics 2010, 29: 775 -
3c
Monfette S.Camm KD.Gorelsky SI.Fogg DE. Organometallics 2009, 28: 944 -
3d
Mathers RT.McMahon KC.Damodaran K.Retarides CJ.Kelley DJ. Macromolecules 2006, 39: 8982 -
3e
Conrad JC.Parnas HH.Snelgrove JL.Fogg DE. J. Am. Chem. Soc. 2005, 127: 11882 -
3f
Hoye TR.Zhao H. Org. Lett. 1999, 1: 1123 -
3g
Nugent WA.Feldman J.Calabrese JC. J. Am. Chem. Soc. 1995, 117: 8992 -
4a
Clavier H.Caijo F.Borre E.Rix D.Boeda F.Nolan SP.Mauduit M. Eur. J. Org. Chem. 2009, 25: 4254 -
4b
Rix D.Caijo F.Laurent I.Boeda F.Clavier H.Nolan SP.Mauduit M. J. Org. Chem. 2008, 73: 4225 -
4c inventors; Mauduit M.,
Laurent I., Clavier H. WO 2008065187.
, Chem. Abstr. 2008, 149, 32434
-
4d
Borre E.Caijo F.Rix D.Crévisy C.Mauduit M. Chem. Today 2008, 26: 89 -
5a
Hong SH.Sanders DP.Lee CW.Grubbs RH. J. Am. Chem. Soc. 2005, 127: 17160 -
5b
Bourgeois D.Pancrazi A.Nolan SP.Prunet J. J. Organomet. Chem. 2002, 643-644: 247