Radical addition of 2-iodoalkanamide or 2-iodoalkanoic acid to alkenols using a water-soluble radical initiator in water. A facile synthesis of γ- lactones

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 519-522

  Yorimitsu, Hideki ^a   Wakabayashi, Katsuyu ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Cyclisation; Lactonisation; Radicals and radical reactions; Solvents and solvent effects

Indexed keywords

ALKENE DERIVATIVE; GAMMA LACTONE DERIVATIVE; HEXANE; IODOACETAMIDE; IODOACETIC ACID; RADICAL; VALERIC ACID DERIVATIVE; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; HEATING; SOLUBILITY; SYNTHESIS;

EID: 0033555662     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02391-0     Document Type: Article

References (21)

1. (a) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media; John Wiley & Sons, Inc.: New York, 1997;
2. (b) Li, C.-J. Chem. Rev. 1993, 93, 2023-2035;
3. (c) Grieco, P. A. Organic Synthesis in Water; Blackie Academic & Professional, London, 1998.
4. Minisci, F. Synthesis 1973, 1-24; Yamazaki, O.; Togo, H.; Nogami, G.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1997, 70, 2519-2523; Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, in press.
5. Minisci, F. Synthesis 1973, 1-24; Yamazaki, O.; Togo, H.; Nogami, G.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1997, 70, 2519-2523; Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, in press.
6. Minisci, F. Synthesis 1973, 1-24; Yamazaki, O.; Togo, H.; Nogami, G.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1997, 70, 2519-2523; Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, in press.
7. Recent examples using water-soluble initiator in polymer chemistry: Morgan, J. D.; Lusvardi, K. M.; Kaler, E. W. Macromol. 1997, 30, 1897-1905; Encinas, M. V.; Lissi, E. A.; Martinez, C. Eur. Polym. J. 1996, 32, 1151-1154; Badey, B.; Boullanger, P.; Delair, T.; Cros, P.; Domard, A.; Pichot, C. Macromol. Chem. Phys. 1996, 197, 3711-3728; Baday, B.; Boullanger, P.; Domard, A.; Cros, P.; Delair, T.; Pichot, C. Macromol. Chem. Phys. 1997, 198, 945-957; Aoki, S.; Morimoto, Y. Colloid Polym. Sci. 1995, 273, 733-739.
8. Recent examples using water-soluble initiator in polymer chemistry: Morgan, J. D.; Lusvardi, K. M.; Kaler, E. W. Macromol. 1997, 30, 1897-1905; Encinas, M. V.; Lissi, E. A.; Martinez, C. Eur. Polym. J. 1996, 32, 1151-1154; Badey, B.; Boullanger, P.; Delair, T.; Cros, P.; Domard, A.; Pichot, C. Macromol. Chem. Phys. 1996, 197, 3711-3728; Baday, B.; Boullanger, P.; Domard, A.; Cros, P.; Delair, T.; Pichot, C. Macromol. Chem. Phys. 1997, 198, 945-957; Aoki, S.; Morimoto, Y. Colloid Polym. Sci. 1995, 273, 733-739.
9. Recent examples using water-soluble initiator in polymer chemistry: Morgan, J. D.; Lusvardi, K. M.; Kaler, E. W. Macromol. 1997, 30, 1897-1905; Encinas, M. V.; Lissi, E. A.; Martinez, C. Eur. Polym. J. 1996, 32, 1151-1154; Badey, B.; Boullanger, P.; Delair, T.; Cros, P.; Domard, A.; Pichot, C. Macromol. Chem. Phys. 1996, 197, 3711-3728; Baday, B.; Boullanger, P.; Domard, A.; Cros, P.; Delair, T.; Pichot, C. Macromol. Chem. Phys. 1997, 198, 945-957; Aoki, S.; Morimoto, Y. Colloid Polym. Sci. 1995, 273, 733-739.
10. Recent examples using water-soluble initiator in polymer chemistry: Morgan, J. D.; Lusvardi, K. M.; Kaler, E. W. Macromol. 1997, 30, 1897-1905; Encinas, M. V.; Lissi, E. A.; Martinez, C. Eur. Polym. J. 1996, 32, 1151-1154; Badey, B.; Boullanger, P.; Delair, T.; Cros, P.; Domard, A.; Pichot, C. Macromol. Chem. Phys. 1996, 197, 3711-3728; Baday, B.; Boullanger, P.; Domard, A.; Cros, P.; Delair, T.; Pichot, C. Macromol. Chem. Phys. 1997, 198, 945-957; Aoki, S.; Morimoto, Y. Colloid Polym. Sci. 1995, 273, 733-739.
11. Recent examples using water-soluble initiator in polymer chemistry: Morgan, J. D.; Lusvardi, K. M.; Kaler, E. W. Macromol. 1997, 30, 1897-1905; Encinas, M. V.; Lissi, E. A.; Martinez, C. Eur. Polym. J. 1996, 32, 1151-1154; Badey, B.; Boullanger, P.; Delair, T.; Cros, P.; Domard, A.; Pichot, C. Macromol. Chem. Phys. 1996, 197, 3711-3728; Baday, B.; Boullanger, P.; Domard, A.; Cros, P.; Delair, T.; Pichot, C. Macromol. Chem. Phys. 1997, 198, 945-957; Aoki, S.; Morimoto, Y. Colloid Polym. Sci. 1995, 273, 733-739.
12. 2O for 10 h in the presence of 1b. In addition to the γ-lactone, a complex mixture containing acids, which were generated by hydrolysis of the ester group, was obtained.
13. Radical additions of alkyl 2-haloalkanoates to alkenes initiated by electron transfer from copper in solvent-free systems have been reported. Metzger, J. O.; Mahler, R.; Francke, G. Liebigs. Ann./Recueil 1997, 2303-2313.
14. Representative experiment for preparation of γ-lactone: A water-soluble radical initiator 1 (0.5 mmol) was added to a solution of 2-iodoacetamide (1.0 mmol) and 5-hexen-1-ol (1.5 mmol) in water (10 mL). The mixture was heated at 75 °C for 16 h. The product was extracted with ethyl acetate (20 mL x 2). The combined organic layers were washed with water, and then dried and concentrated. The residue was purified by silica gel column chromatography to give γ-lactone in 95% yield.
15. The solution became acidic as the reaction proceeded.
16. Stirling, C. J. M. J. Chem. Soc. 1960, 255-262; Zaugg, H. E.; Michaels, R. J. J. Org. Chem. 1963, 28, 1801-1805.
17. Stirling, C. J. M. J. Chem. Soc. 1960, 255-262; Zaugg, H. E.; Michaels, R. J. J. Org. Chem. 1963, 28, 1801-1805.
18. Radical atom transfer reactions followed by irreversible ionic reactions have been reported. Curran, D. P.; Ko, S.-B. Tetrahedron Lett. 1998, 39, 6629-6632; Joung, M. J.; Ahn, J. H.; Lee, D. W.; Yoon, N. M. J. Org. Chem. 1998, 63, 2755-2757; Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465-5466.
19. Radical atom transfer reactions followed by irreversible ionic reactions have been reported. Curran, D. P.; Ko, S.-B. Tetrahedron Lett. 1998, 39, 6629-6632; Joung, M. J.; Ahn, J. H.; Lee, D. W.; Yoon, N. M. J. Org. Chem. 1998, 63, 2755-2757; Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465-5466.
20. Radical atom transfer reactions followed by irreversible ionic reactions have been reported. Curran, D. P.; Ko, S.-B. Tetrahedron Lett. 1998, 39, 6629-6632; Joung, M. J.; Ahn, J. H.; Lee, D. W.; Yoon, N. M. J. Org. Chem. 1998, 63, 2755-2757; Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465-5466.
21. Reducing the amount of NaI (0.2 mmol) resulted in formation of γ-lactone 18 in only 39% yield.