Comparison of the one-bond nucleophilicities of monomethyl- and dimethyl-substituted 1,3-butadienes

Liebigs Annales

Volumn , Issue 12, 1996, Pages 2015-2018

  Mayr, Herbert ^a,b   Hartnagel, Manfred ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

1,3 dienes; Allyl cations; Benzhydryl cations; Enthalpy relationships, linear free; Kinetics

Indexed keywords

EID: 0142050716     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619961211     Document Type: Review

References (29)

1. [1a] R. Huisgen, R. Schug, J. Am. Chem. Soc. 1976, 98, 7819-7821.
2. [1b] K. N. Houk, L. L. Munchausen, J. Am. Chem. Soc. 1976, 98, 937-946.
3. [2a] W. K. Chwang, V. J. Nowlan, T. T. Tidwell, J. Am. Chem. Soc. 1977, 99, 7233-7238.
4. [2b] W. K. Chwang, P. Knittel, K. M. Koshy, T. T. Tidwell, J. Am. Chem. Soc. 1977, 99, 3395-3401.
5. H. Mayr, Angew. Chem. 1990, 102, 1415-1428;
6. Angew. Chem. Int. Ed. Engl. 1990, 29, 1371-1384.
7. [4a] J. Sauer, R. Sustmann, Angew. Chem. 1980, 92, 773-801;
8. Angew. Chem. Int. Ed. Engl. 1980, 19, 779-807.
9. [4b] F. Kataoka, N. Shimizu, S. Nishida, J. Am. Chem. Soc. 1980, 102, 711-716.
10. [4c] F. Jensen, C. S. Foote, J. Am. Chem. Soc. 1987, 109, 6376-6385.
11. [4d] R. Brückner, R. Huisgen, Tetrahedron Lett. 1994, 35, 3285-3288.
12. H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-1010;
13. Angew. Chem. Int. Ed. Engl., 1994, 33, 938-957.
14. [6a] C. D. Ritchie, Acc. Chem. Res. 1972, 5, 348-354.
15. [6b] C. D. Ritchie, Can. J. Chem. 1986, 64, 2239-2250.
16. [7a] H. Mayr, R. Schneider, B. Irrgang, C. Schade, J. Am. Chem. Soc. 1990, 112, 4454-4459.
17. [7b] R. Pock, H. Mayr, Chem. Ber. 1986, 119, 2497-2509.
18. [7c] H. Mayr in Cationic Polymerization: Mechanism, Synthesis and Applications (Ed.: K. Matyjaszewski), M. Dekker, New York, 1996, p. 51-136.
19. H. Mayr, W. Striepe, J. Org. Chem. 1985, 50, 2995-2998.
20. H. Mayr, R. Schneider, C. Schade, J. Bartl, R. Bederke, J. Am. Chem. Soc. 1990, 112, 4446-4454.
21. H. Mayr, R. Schneider, U. Grabis, J. Am. Chem. Soc. 1990, 112, 4460-4467.
22. [5].
23. H. Mayr, W. Förner, P. v. R. Schleyer, J. Am. Chem. Soc. 1979, 101, 6032-6040.
24. J. B. Pedley, R. D. Naylor, S. P. Kirby, Thermochemical Data of Organic Compounds, 2nd ed, Chapman and Hall, London, 1986.
25. R. L. Frank, R. D. Emmick, R. S. Johnson, J. Am. Chem. Soc. 1947, 69, 2313-2317.
26. H. J. Backer, J. Strating, C. M. H. Kool, Rec. Trav. Chim. Pays-Bas. 1939, 58, 778-784.
27. D. Craig, J. Am. Chem. Soc. 1943, 65, 1006-1013.
28. G. B. Bachman. C. G. Goebel, J. Am. Chem. Soc. 1942, 64, 787-790.
29. H. Mayr, G. Hagen in Encyclopedia of Reagents for Organic Synthesis Vol. 8 (Ed.: L. A. Paquette), John Wiley and Sons, Chichester, 1995, p. 5552-5554.