Dipole-Stabilized Carbanions: Secondary (α-Lithioalkyl)alky lamine Synthetic Equivalents from N,N-Dialkyl-2,2-diethylbutyramides

Journal of Organic Chemistry

Volumn 46, Issue 21, 1981, Pages 4316-4317

  Reitz, David B ^a   Beak, Peter ^b   Tse, Anthony ^b  

^a MONSANTO COMPANY   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000311992     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00334a052     Document Type: Article

References (15)

1. For a review of dipole-stabilized carbanions see P. Beak and D. B. Reitz, Chem. Rev., 78, 275 (1978).
2. Routes to a-lithio amine synthetic equivalents not based on carboxamides include: (a) primary and activated secondary derivatives from isonitriles, D. Stafforst and U. Schollkopf, Justus Liebigs Ann. Chem., 28 (1980), and references cited therein;
3. primary derivatives from imines, T. Kauffmann, H. Berg, E. Koppelmann, and D. Kuhlmann, Ber., 110, 2659 (1977), and references cited therein;
4. primary, secondary and tertiary derivatives from nitroso amines, D. Seebach and W. Wykypiel, Synthesis, 423 (1979), and references cited therein.
5. P. Beak and R. Farney, J. Am. Chem. Soc., 95, 4771 (1973); D. Seebach and W. Lubosch, Angew. Chem., Int. Ed. Engl., 15, 313 (1976); P. Beak, B. G. McKinnie, and D. B. Reitz, Tetrahedron Lett., 1839 (1977); R. Schlecker and D. Seebach, Helv. Chim. Acta, 60,1459 (1977).
6. R. Schlecker, D. Seebach, and W. Lubosch, Helv. Chim. Acta, 61, 512 (1978); T. Hassel and D. Seebach, J. Am. Chem. Soc., 61, 2237 (1978).
7. J. C. L. Armande and U. K. Pandit, Tetrahedron Lett., 897 (1977);
8. D. Seebach and T. Hassel, Angew. Chem., Int. Ed. Engl., 17, 274 (1978);
9. T. L. Macdonald, J. Org. Chem., 45, 193 (1980);
10. J. C. L. Armande and U. K. Pandit, Reel. Trav. Chim. Pays-Bas., 99, 87 (1980);
11. J.-J. Lohmann, D. Seebach, M. A. Syfrig, and M. Yoshifuji, Angew. Chem., Int. Ed. Engl., 20,128 (1981). See A. N. Tischler and M. H. Tischler, Tetrahedron Lett., 3407 (1978), for cases of (a-lithio-benzyl)lithioamide and (a-lithioallyl)lithioamide derivatives.
12. A. I. Meyers and W. Ten Hoeve, J. Am. Chem. Soc., 102, 7125 (1980).
13. J. Hine, “Structural Effects on Equilibria in Organic Chemistry”, Wiley, New York, 1975, pp 229-234; M. S. Newman, “Steric Effects in Organic Chemistry”, M. S. Newman, Ed., Wiley, New York, 1956, pp 201-248; A. Panaye, J. A. MacPhee, and J.-E. Dubois, Tetrahedron Lett., 3485 (1980).
14. C. Lion, J.-E. Dubois, J. A. MacPhee, and Y. Bonzougou [Tetrahedron, 35, 2077 (1979)] have recently reported that sterically hindered esters with substitution comparable to 1-4 undergo dealkylation on treatment with n-propyllithium at 0 °C.
15. For examples of analogous thioesters and esters see: D. B. Reitz, P. Beak, R. F. Farney, and L. S. Helmick, J. Am. Chem. Soc., 100, 5428 (1978); P. Beak and L. G. Carter, J. Org. Chem., 46, 2363 (1981).