Abstract
Kinetic separation of trans-limonene oxide and trans-carvomenthene oxide was achieved in high yield by selective ring opening of their cis-epoxides in the presence of InCl3 catalyst in water. Catalytic activity of InCl3 was conserved up to 10 cycles. Nucleophilic addition of methanol in presence of InCl3 was also selective as cis-epoxides preferentially reacted leaving behind trans-epoxides, which were separated by fractional distillation.
The kinetic separation of trans-limonene oxide and trans-carvomenthene oxide was achieved in high yield (97%) by selective ring opening of the corresponding cis-oxides in a reaction of 1:1 mixture of these epoxides with water or methanol in the presence of InCl3 catalyst.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bauer K, Garbe D and Surburg H 1997 In Common fragrance and flavour materials, preparation, properties and uses (New York: Wiley VCH)
(a) Comins D, Weltzien L G and Salvador J M 1994 Synlett 11 972; (b) Chrisman W, Camara J N, Marcellini K, Singaram B, Goralski C T, Hasha D L, Rudolf P R, Nicholson L W and Borodychuk K K 2001 Tetrahedron Lett. 42 5805
Lebel H and Jacobsen E N 1998 J. Org. Chem. 63 9624
(a) Byrne C M, Allen S D, Lobkovsky E B and Coates G W 2004 J. Am. Chem. Soc. 126 11404; (b) Jeske R C, Diciccio A M and Coates G W 2007 J. Am. Chem. Soc. 129 11330
(a) Besse P and Veschambre H 1994 Tetrahedron 50 8885; (b) Churing S V and Betchinger F 1992 Chem. Rev. 92 873; Archelas A and Furstoss R 1997 Annu. Rev. Microbiol. 51 491
van der Werf M J, Jongejan H and Maurice Franssen C R2001 Tetrahedron Lett. 42 5521
Steiner D, Ivison L, Goralski C T, Appell R B, Gojkovic J R and Singaram B 2002 Tetrahedron: Asymmetry 13 2359
Cole-Hamilton D J, Salles L, Nixon A F, Russell N C, Clarke R and Pogorzelec P 1999 Tetrahedron: Asymmetry 10 1471
Tokunaga M, Larrow J F, Kakiuchi F and Jacobsen E N 1997 Science 277 936
Bart Dioos M L and Pierre Jacobs A 2003 Tetrahedron Lett. 44 4715
Bettadaiah B K and Srinivas P 2004 J. Photochem. Photobiol. A167 137
(a) Loh T P and Chua G L 2006 Chem. Commun. 2739; (b) Sun H B, Chen W L, Sun Y H, Qin P and Qi X 2011 Adv. Mater. Res. 396–398 2416
Royals E E and Leffingwell J C 1966 J. Org. Chem. 31 1937
Sanseverino A M, da Silva F M, Jones J J and de Mattos M C S 2000 J. Braz. Chem. Soc. 11 381
Gurudutt K N, Rao S and Srinivas P 1992 Flav. Fragr. J. 7 343
Acknowledgements
The author SCSK thanks the University Grants Commission, New Delhi for Junior Research Fellowship. The authors also thank Mr. Shivaswamy, Central Instruments Facility and Services department, CFTRI, Mysore for GC-MS analysis.
Author information
Authors and Affiliations
Corresponding author
Additional information
Supplementary information
The electronic supplementary material contains1H NMR, 13C NMR and mass spectra of compounds 1b, 1c, 1d, 2b, 2c and 2d, which can be seen in www.ias.as.in/chemsci.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
SANTOSH KUMAR, S.C., MANJUNATHA, J.R., SRINIVAS, P. et al. Eco-friendly kinetic separation of trans-limonene and carvomenthene oxides. J Chem Sci 126, 875–880 (2014). https://doi.org/10.1007/s12039-014-0633-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-014-0633-9