Synthesis of 1-arylalkyl N,N-dialkylcarbamates by lithiation and substitution of benzylic-type carbamates

Synthesis (Germany)

Volumn 1982, Issue 12, 1982, Pages 1045-1048

  Hoppe, Dieter ^a   Brönneke, Alfons ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

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EID: 84984247528     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1982-30058     Document Type: Article

References (21)

1. Lithiated alkyl benzyl ethers: G. Wittig, L. Löhmann, Justus Liebigs Ann. Chem. 550, 260 (1942).
2. G. Wittig, P. Davis, G. König, Chem. Ber. 84, 627 (1951).
3. For references to more recent work: H. d'Orchymont, M. P. Goeldner, J. P. Biellmann, Tetrahedron Lett. 23, 1727 (1982).
4. Lithiated benzyl imidates: A. R. Katritzky, N. K. Ponkshe, Tetrahedron Lett. 22, 1215 (1981).
5. Review: B. J. Wakefield, The Chemistry of Organolithium Compounds, Pergamon Press, Oxford, 1974, p. 34.
6. Lithiated benzyl trialkylsilyl ethers: A. Wright, R. West, J. Am. Chem. Soc. 96, 3214, 3222, 3227 (1976).
7. A. I. Meyers, A. L. Campbell, Tetrahedron Lett. 1979, 4155.
8. M. K. Yeh, J. Chem. Soc. Perkin Trans. 1 1981, 1652.
9. For a lithiated benzyl ester (R'= 2, 4, 6-triisopropylbenzoyl in 2), see: P. Beak, L. G. Carter, J. Org. Chem. 46, 2363 (1981).
10. D. Hoppe, R. Hanko, A. Brfjnneke, Angew. Chem. 92, 637 (1980);
11. Angew. Chem. Int. Ed. Engl. 18, 625 (1980).
12. D. Hoppe, R. Hanko, A. Bronneke, F. Lichtenberg, Angew. Chem. 93, 1106 (1981);
13. Angew. Chem. Int. Ed. Engl. 20, 1024 (1981).
14. R. Hanko, D. Hoppe, Angew. Chem. 94, 378 (1982);
15. Angew. Chem. Int. Ed. Engl. 21, 372 (1982).
16. N. Meyer, D. Seebach, Chem. Ber. 113, 1304 (1980).
17. C. A. Panetta, A. S. Dixit, Synthesis 1981, 59.
18. For leading references: P. Beak, R. A. Brown, J. Org. Chem. 47, 34 (1982).
19. R. F. Atkinson et al., J. Org. Chem. 46, 2804(1981), and references cited therein.
20. L. A. Paquette, W. E. Fristad, D. S. Dime, T. R. Bailey, J. Org. Chem. 45, 3017 (1980).
21. J. Herzog, Ber. Dtsch. Chem. Ges. 40, 1831 (1907).