Alkylation of alkenes: Ethylaluminum sesquichloride-mediated hydro-alkyl additions with alkyl chloroformates and di-tert-butylpyrocarbonate

Journal of the American Chemical Society

Volumn 126, Issue 33, 2004, Pages 10319-10330

  Biermann, Ursula ^a   Metzger, Jürgen O ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CHEMICAL BONDS; ESTERS; HYDRIDES; OLEFINS; OLEIC ACID;

ALKYL CHAINS; ALKYL CHLOROFORMATES; CARBENIUM ION;

ALKYLATION;

ALKENE; ALKYL GROUP; ALUMINUM DERIVATIVE; CARBENE; CARBENIUM ION; CARBONIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CATION; CHLORIDE; CHLOROFORMIC ACID ETHYL ESTER; CYCLOALKENE; DI TERT BUTYLPYROCARBONATE; ESTER; ETHYLALUMINUM SESQUICHLORIDE; OLEIC ACID; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID;

ADDITION REACTION; ALKYLATION; ARTICLE; CHEMICAL REACTION; COVALENT BOND; DOUBLE BOND; HYDRIDE TRANSFER; HYDRO ALKYL ADDITION; QUANTUM YIELD; SYNTHESIS;

EID: 4143102504     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048904y     Document Type: Article

References (58)

1. Industrial and Laboratory Alkylations; Albright, L. F., Goldsby, A. R., Eds.; ACS Symposium Series 1977; American Chemical Society: Washington, DC, 1978.
2. Metzger, J. O. J. Prakt. Chem. 1990, 332, 767-781.
3. Metzger, J. O.; Bangert, F. Fat Sci. Technol. 1995, 97, 7-9.
4. (a) Pines, H. In The Chemistry of Catalytic Hydrocarbon Conversions; Academic Press: New York, 1981; pp 50-58.
5. (b) Nenitzescu, C. D. In Carbonium Ions; Olah, G. A., von R. Schleyer, P., Eds.; Wiley: New York, 1970; Vol. II, pp 463-520 (at p 504).
6. (c) Olah, G. A.; Farooq O.; Krishnamurthy, V. V.; Prakash, G. K. S.; Laali, K. J. Am. Chem. Soc. 1985, 107, 7541-7545.
7. (d) Olah, G. A.; Batamack, P.; Deffieux, D.; Torok, B.; Wang, Q.; Molnar, A.; Prakash, G. K. S. Appl. Catal., A 1996, 146, 107-117.
8. (e) Olah, G. A.; Marinez, E.; Torok, B.; Prakash, G. K. S. Catal. Lett. 1999, 61, 105-110.
9. Kennedy, P.; Maréchal, E. In Carbocationic Polymerization; Wiley-Interscience: New York, 1982; p 82.
10. Olah, G. A.; Kuhn, S. J.; Barnes, D. G. J. Org. Chem. 1964, 29, 2685-2687.
11. (a) Mayr, H. Angew. Chem. 1981, 93, 202-204; Angew. Chem., Int. Ed. Engl. 1981, 20, 184-186.
12. (a) Mayr, H. Angew. Chem. 1981, 93, 202-204; Angew. Chem., Int. Ed. Engl. 1981, 20, 184-186.
13. (b) Mayr, H.; Striepe, W. J. Org. Chem. 1983, 48, 1159-1165.
14. Mayr, H. Angew. Chem. 1990, 102, 1415-1428; Angew. Chem., Int. Ed. Engl. 1990, 29, 1371-1384.
15. Mayr, H. Angew. Chem. 1990, 102, 1415-1428; Angew. Chem., Int. Ed. Engl. 1990, 29, 1371-1384.
16. (a) Mayr, H.; Schneider, R.; Schade, C.; Bartl, J.; Bederke, R. J. Am. Chem. Soc. 1990, 112, 4446-4454.
17. (b) Mayr, H.; Schneider, R.; lrrgang, B.; Schade, C. J. Am. Chem. Soc. 1990, 112, 4454-4459.
18. (a) Mayr, H.; Patz, M. Angew. Chem. 1994, 106, 990-1010; Angew. Chem., Int. Ed. Engl. 1994, 33, 938-957;
19. (a) Mayr, H.; Patz, M. Angew. Chem. 1994, 106, 990-1010; Angew. Chem., Int. Ed. Engl. 1994, 33, 938-957;
20. (b) Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Kempf, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500-9512.
21. Petrov, A. A.; Leets, K. V. Zh. Obshch. Khim. 1956, 26, 1113, Chem. Abstr. 1956, 50, 11936d.
22. Petrov, A. A.; Leets, K. V. Zh. Obshch. Khim. 1956, 26, 1113, Chem. Abstr. 1956, 50, 11936d.
23. Miller, V. A. J. Am. Chem. Soc. 1947, 69, 1764-1768.
24. Schmerling, L. J. Am. Chem. Soc. 1953, 75, 6217-6222.
25. Kevill, D. N. In The Chemistry of Acyl Halides, Chloroformate Esters and Related Compounds; Patai, S., Ed.; Wiley: London 1972, pp 425-433.
26. (a) Olah, G. A.; Olah, J. A. In Carbonium Ions; Olah, G. A., von R. Schleyer, P., Eds.; Wiley: New York, 1970; Vol. II, pp 715-782 (at p 765).
27. (b) Kirmse, B. Top Curr. Chem. 1979, 80, 125-311 (at p 172).
28. Beak, P. Acc. Chem. Res. 1976, 9, 230-236.
29. Friedel, C.; Crafts, J. M. C. R. Seances Acad. Sci. 1877, 84, 1450-1454.
30. Rennie, E. H. J. J. Chem. Soc. 1882, 41, 33.
31. (a) Biermann, U.; Friedt, W.; Lang, S.; Lühs, W.; Machmüller, G.; Metzger, J. O.; Rüsch gen. Klaas, M.; Schäfer, H. J.; Schneider, M. P. Angew. Chem. 2000, 112, 2292-2310; Angew. Chem., Int. Ed. 2000, 39, 2206-2224.
32. (a) Biermann, U.; Friedt, W.; Lang, S.; Lühs, W.; Machmüller, G.; Metzger, J. O.; Rüsch gen. Klaas, M.; Schäfer, H. J.; Schneider, M. P. Angew. Chem. 2000, 112, 2292-2310; Angew. Chem., Int. Ed. 2000, 39, 2206-2224.
33. (b) Biermann, U.; Metzger, J. O. Top. Catal. 2004, 27, 119-130.
34. (c) Eissen, M.; Metzger, J. O.; Schmidt, E.; Schneidewind, U. Angew. Chem. 2002, 114, 402-425; Angew. Chem., Int. Ed. 2002, 41, 414-436.
35. (c) Eissen, M.; Metzger, J. O.; Schmidt, E.; Schneidewind, U. Angew. Chem. 2002, 114, 402-425; Angew. Chem., Int. Ed. 2002, 41, 414-436.
36. Syntheses of Novel Fatty Acid Derivatives; Knothe, G., Derksen, J. T. P., Eds.; American Oil Chemists Society: Champaign, IL, 1999.
37. Biermann, U.; Fürmeier, S.; Metzger, J. O. In Oleochemical Manufacture and Applications; Gunstone, F. D., Hamilton, R. J., Eds.; Sheffield Academic Press and CRC Press: Boca Raton, FL, 2001, 266-299.
38. Kinsman, D. V. In Fatty Acids in Industry; Johnson, R. W., Fritz, E., Eds.; Marcel Dekker: New York, 1989; pp 233-276.
39. Johnson, R. W., Jr.; Cantrell, R. R. In Kirk Othmer Encyclopedia of Chemical Technology, 4th ed.; New York: Wiley, 1993; Vol. 5, 189-192.
40. Technical Data Sheet, Emersol 874 Isostearic Acid, Henkel Coorporation: Gulph Mills, PA, 1999.
41. For a preliminary account of our results, see: Biermann, U.; Metzger, J. O. Angew. Chem., Int. Ed. 1999, 38, 3675-3677.
42. Fordyce, C. R.; Johnson, J. R. J. Am. Chem. Soc. 1933, 55, 3368-3372.
43. (a) Handa, S.; Floss. H. G. Chem. Commun. 1997, 153-154.
44. (b) Floss, H. G. Nat. Prod. Rep. 1997, 14, 433-452.
45. Snider, B. B.; Rodini, D. J.; Karras, M.; Kirk, T. C.; Deutsch, E. A.; Cordova, R.; Price, R. T. Tetrahedron 1981, 37, 3927-3934.
46. Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Soc. 1982, 104, 555-563.
47. Keating, J. T.; Skell, P. S. In Carbonium Ions; Olah, G. A., Schleyer, P. v. R., Eds.; Wiley: New York, 1970, Vol. II, pp 573-653.
48. Fry, J. L.; Karabatsos, J. J. In Carbonium Ions; Olah, G. A., Schleyer, P. v. R., Eds.; Wiley: New York, 1970, Vol. II, pp 521-571.
49. Siehl, H.-U.; Vrcek, V.; Kronja, O. J. Chem. Soc., Perkin Trans. 2 2002, 106-113.
50. Lenoir, D.; Siehl, H.-U. In Houben-Weyl; Georg Thieme-Verlag: Stuttgart, 1990, Vol. E19c, p 264.
51. Vrcek, V.; Siehl, H.-U.; Kronja, O. J. Phys. Org. Chem. 2000, 13, 616-6.
52. Vrcek, V.; Saunders, M.; Kronja, O. J. Org. Chem. 2003, 68, 1859-1866.
53. Petersen, S.; Piepenbrink, H.-F. In Houben-Weyl, 4th ed.; Georg Thieme-Verlag: Stuttgart, 1952; Vol. 8, 101-104.
54. Bazyl'chik, V. V.; Samitov, Y. Y.; Ryabushkina, N. M. J. Appl. Spectrosc. 1980, 32(5), 543-548.
55. Balzer, T.; Budzikiewicz, H. Z. Naturforsch. 1987, 42b, 1367-1368.
56. Goodrich, B. S.; Roberts, D. S. Aust. J. Chem. 1971, 24, 4, 153-159.
57. Jacob, J.; Zeman, A. Z. Naturforsch. 1970, 25b, 1438-1447.
58. Schlenk, W. In Houben-Weyl, 4th ed.; Georg Thieme-Verlag: Stuttgart, 1958; Vol 1/1, p 391.