High regioselectivity in the Diels-Alder reaction of a surfactant 1,3-diene with a surfactant dienophile resulting from a short tether between their functional groups and head groups

Tetrahedron Letters

Volumn 40, Issue 45, 1999, Pages 7871-7874

  Su, Dan ^a   Jaeger, David A ^a  

^a UNIVERSITY OF WYOMING   (United States)

Author keywords

Diels Alder reactions; Micellar systems; Regiocontrol; Surfactants

Indexed keywords

ALKADIENE; FUNCTIONAL GROUP; SURFACTANT;

ARTICLE; CHEMICAL MODIFICATION; MICELLE; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0033527591     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01637-8     Document Type: Article

References (19)

1. Grieco, P. A., Ed. Organic Synthesis in Water; Blackie Academic and Professional: London, 1998.
2. For examples, see: (a) Engberts, J. B. F. N. Pure Appl. Chem. 1995, 67, 823.
3. (b) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741.
4. (c) Otto, S.; Engberts, J. B. F. N.; Kwak, J. C. T. J. Am. Chem. Soc. 1998, 120, 9517.
5. (d) Rideout, D. C.; Breslow, R. J. Am. Chem. Soc. 1980, 102, 7816.
6. (e) Braun, R.; Schuster, F.; Sauer, J. Tetrahedron Lett. 1986, 27, 1285.
7. (f) Diego-Castro, M. J.; Hailes, H. C. J. Chem. Soc., Chem. Commun. 1998, 1549.
8. (g) Garner, P. P. In Ref. 1, p. 1, and references cited therein.
9. (a) Jaeger, D. A.; Su, D. Tetrahedron Lett. 1999, 40, 257.
10. (b) Jaeger, D. A.; Wang, J. Tetrahedron Lett. 1992, 33, 6515.
11. (c) Jaeger, D. A.; Wang, J. J. Org. Chem. 1993, 58, 6745.
12. (d) Jaeger, D. A.; Shinozaki, H.; Goodson, P. A. J. Org. Chem. 1991, 56, 2482.
13. (e) Jaeger, D. A.; Wang, J.; Goodson, P. A. J. Crystallogr. Spectrosc. Res. 1993, 23, 955.
14. 13C NMR.
15. Ramadas, K.; Srinivasan, N. Synth. Commun. 1995, 25, 227.
16. Reich, H. J.; Reich, I. E.; Yelm, K. E.; Holladay, J. E.; Gschneidner, D. J. Am. Chem. Soc. 1993, 115, 6625.
17. 2:MeOH; flow rate=1.0 mL/min; retention times=5.7 min for 14 and 4.2 min for 15.
18. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
19. Kahn, S. D.; Pau, C. F.; Overman, L. E.; Hehre, W. J. J. Am. Chem. Soc. 1986, 108, 7381.