Lewis acid complexed heteroatom carbanions; synthesis of some α-pyridyl alcohols

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 8, 1991, Pages 570-571

  Kessar, Satinder V ^a   Singh, Paramjit ^a   Singh, Kamal Nain ^a   Dutt, Mahesh ^a  

^a PANJAB UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049087567     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39910000570     Document Type: Article

References (18)

1. H.Y. Yale, Pyridine and its Derivatives, 1961, E. Klingsberg, Interscience, New York
2. N. Spencer, D. Papa, E. Schwenk and M. Sherlock, J. Am. Chem. Soc., 1951, 73, 3856
3. Comprehensive Heterocyclic Chemistry, 1984, 2, For a discussion of the problems encountered in α-metallation of pyridine see: ed. A. R. Katritzky, C. W. Rees, Pergamon Press Ltd., Oxford
4. D. Price, B. Iddon and B.J. Wakefield, Bromine Compounds: Chemistry and Applications, 1988, Elsevier, Amsterdam Lithiation is possible in the presence of stabilising substituents on the pyridine nucleus;
5. F. Marsais, G. Le Nard and G. Queguiner, Synthesis, 1982, 235, For use of hexafluoroacetone in metallation of pyridines see:
6. S.L. Taylor, D.Y. Lee and J.C. Martin, J. Org. Chem., 1983, 48, 4157
7. R.A. Abramovitch and A.R. Vinutha, J. Chem. Soc., (c), 1969, 2104
8. C.E. Crawforth and C.A. Russell, Chem. Commun., 1970, 1406, Emmert reaction or its modified version gives modest yields of α-pyridyl alcohols.
9. 2, may have some carbene character.
10. A.C. Clarke, S. McNamara and O. Meth-Cohn, Tetrahedron Lett., 1974, 27, 2373, See the preceeding Communication. The intermediate This is in conformity with earlier results using lithium diiso-propylamide (LDA);
11. G.R. Newkome and D.C. Hager, J. Org. Chem., 1982, 47, 599
12. A.E. Tschitschibabin, Berichte, 1904, 37, 1370
13. H.L. Lochte, P.F. KruseJr. and E.N. Wheeler, J. Am. Chem. Soc., 1953, 75, 4477
14. V.K. Goel, R.K. Pandey and B.C. Joshi, J. Ind. Chem. Soc., 1977, 54, 538
15. J. Bosch, R. Grandos, R. Llohera and D. Mauleon, An. Quim., Ser. C, 1981, 77, 166
16. R.A. Abramovitch, F.M. Smith, E.E. Knaus and M. Saha, J. Org. Chem., 1972, 37, 1960
17. H.C. Brown and N.N. Joshi, J. Org. Chem., 1988, 53, 4059
18. K. Rein, M. Goicoechea-Pappas, T.V. Anklekar, G.C. Hart, G.A. Smith and R.E. Gawley, J. Am. Chem. Soc., 1989, 111, 2211