DOI QR코드

DOI QR Code

Concomitant Addition and Acetalization of α,β-Unsaturated Aldehydes with Diols

  • Jeon, Kyu-Ok (Department of Chemistry, Kangwon National University) ;
  • Yu, Ji-Sook (Department of Chemistry, Kangwon National University) ;
  • Lee, Chang-Kiu (Department of Chemistry, Kangwon National University)
  • Published : 2004.11.20

Abstract

${\alpha},{\beta}$-Unsaturated aldehydes such as acrolein and crotonaldehyde were reacted with diols in the presence of conc. sulfuric acid to give products of which concomitant addition to C-C double bond and acetalization took place. Boron trifluoride etherate and titanium tetrachloride gave only acetalization products.

Keywords

References

  1. Jeon, K. O.; Yu, J. S.; Lee, C. K. Bull. Korean Chem. Soc. 2003, 24, 1845-1848. https://doi.org/10.5012/bkcs.2003.24.12.1845
  2. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370. https://doi.org/10.1021/ja0214882
  3. Goldberg, S. D.; Grubbs, H. Angew. Chem. Int. Ed. 2002, 41, 807-810. https://doi.org/10.1002/1521-3773(20020301)41:5<807::AID-ANIE807>3.0.CO;2-V
  4. Chavan, S. P.; Sharma, P.; Rama, K. G.; Thakkar, M. Tetrahedron Lett. 2003, 44, 3001-3003. https://doi.org/10.1016/S0040-4039(03)00387-3
  5. Chavan, S. P.; Sharma, A. K. Synlett 2001, 5, 667-669.
  6. Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182-2184. https://doi.org/10.1021/ja00241a047
  7. Weidner-Wells, M. A.; Fraga-Spano, S. A.; Turchi, I. J. J. Org. Chem. 1998, 63, 6319-6328. https://doi.org/10.1021/jo9807621
  8. Lu, T.-J.; Yang, J.-F.; Sheu, L.-J. J. Org. Chem. 1995, 60, 7701-7705. https://doi.org/10.1021/jo00128a054
  9. Yanagisawa, A.; Habaue, S.; Yamamoto, H. J. Am. Chem. Soc. 1989, 111, 366-368. https://doi.org/10.1021/ja00183a056
  10. Kwak, K. C.; Oh, H.; Yun, Y.-G.; Kim, B.-H.; Lee, Y.-H.; Chai, K. Y. Bull. Korean Chem. Soc. 2002, 23, 157-159. https://doi.org/10.5012/bkcs.2002.23.1.157
  11. Lu, T.-J.; Cheng, S.-M.; Sheu, L.-J. J. Org. Chem. 1998, 63, 2738-2741. https://doi.org/10.1021/jo972048+
  12. Yamashita, N.; Nishii, Y.; Maeshima, T J. Polymer Sci. Polymer Lett. 1979, 17, 521-526. https://doi.org/10.1002/pol.1979.130170808
  13. Sumitomo, H.; Okada, M.; Ito, H. J. Polymer Sci. Polymer Chem. 1971, 9, 3115-3127.
  14. Moriya, O.; Urata, Y.; Endo, T. J. Polymer Sci. Part A: Polymer Chem. 1991, 29, 1501-1505. https://doi.org/10.1002/pola.1991.080291014
  15. VanAllan, J. A. Org. Syn. Col. Vol. IV 1963, 21-22.
  16. Piasecki, A.; Burczyk, B. J. Prakt. Chem. 1985, 327, 543-554. https://doi.org/10.1002/prac.19853270404
  17. Ponde, D. E.; Deshpande, V. H.; Bulbule, V. J.; Sudalai, A.; Gajare, A. S. J. Org. Chem. 1998, 63, 1058-1063. https://doi.org/10.1021/jo971404l
  18. Laskar, D. D.; Prajapati, D.; Sandhu, J. S. Chem. Lett. 1999, 12, 1283-1284.
  19. Piasecki, A. Monatshefte fuer Chemie 1986, 117, 1287-1293. https://doi.org/10.1007/BF00810874
  20. Lu, T.-J.; Yang, J.-F.; Sheu, L.-J. J. Org. Chem. 1995, 60, 2931-2934. https://doi.org/10.1021/jo00114a055
  21. Pihlaja, K.; Kleinpeter, E. Carbon-13 NMR Chemical Shifts in Structural and Stereochemical Analysis; VCH: New York, 1994; pp 91-92.

Cited by

  1. Concomitant Addition and Acetalization of ?,?-Unsaturated Aldehydes with Diols. vol.36, pp.13, 2005, https://doi.org/10.1002/chin.200513065