Tandem Directed Metalation Reactions. Short Syntheses of Polycyclic Aromatic Hydrocarbons and Ellipticine Alkaloids

Journal of the American Chemical Society

Volumn 102, Issue 4, 1980, Pages 1457-1460

  Watanabe, M ^a   Snieckus, V ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ELLIPTICINE DERIVATIVE;

EDITORIAL; TANDEM METALATION REACTION;

EID: 0018837895     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00524a059     Document Type: Letter

References (46)

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36. Entry 5-benz[a]anthracene (58%, mp 156-158 °C, lit. mp 158-159 °C); entry 7 dlbenz[a,c]anthracene (45%, mp 207 °C, lit. mp 205 °C); entry 11-dibenz[a,h]anthracene (85%, mp 267-268 °C, lit. mp 262-263 °C); entry 12-benzo[a]naphthacene (45%, mp 266-267 °C, lit. mp 263-264 °C). All literature melting points refer to those given in E. Clar, “Polycyclic Hydrocarbons” Vol. 2, Academic Press, New York, 1964.
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39. We thank Professor Joule, Manchester University, for informing us of a new, substantially different route to compounds of the type 11 completed In his laboratory: D. A. Taylor, M. M. Baradarani, S. J. Martinez, and J. A. Jouie, J. Chem. Res., In press; see also Int. Congr. Heterocyci. Chem., 7th, 1979, Abstr. T1445P4 (1979).
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41. Identity was established by melting point, mixture melting point, and spectral comparison with an authentic sample kindly provided by Drs. J. Bergman and R. Carlsson, Royal Institute of Technology, Stockholm, Sweden.
42. Compounds 12a (mp 153 °C) and 12b (mp 216-217 °C) were characterized by melting point, mixture melting point, and IR, NMR, and mass spectral comparison with authentic samples: J. A. Campbell, R. W. Koch, J. V. Hay, and M. A. Ogliaruso, J. Org. Chem., 39, 146 (1974); J. Rigaudy, M.-C. Perlat, D. Simon, and N. K. Cuong, Bull. Soc. Chim. Fr., 493 (1976). We thank Dr. S. O. de Silva for these results.
43. Related ortho-lithiated arylcarbinol amine anions have been generated from reaction of W.W-dlmethylbenzamides with 2 equiv of alkyllithium reagents: L. Barsky, H. W. Gschwend, J. McKenna, and H. R. Rodriguez, J. Org. Chem., 41, 3651 (1976). See also D. W. Slocum and W. Achermann, J. Chem. Soc., Chem. Commun., 968 (1974).
44. P. G. Sammes and D. J. Dodsworth, J. Chem. Soc., Chem. Commun., 33 (1979).
45. We have also found that anthraquinone is produced in 74% yield when a solution of ortho-lithiated W.W-dlethylbenzamide is warmed to room temperature overnight: S. O. de Silva and V. Snieckus, unpublished results; see also D. W. Slocum and P. L. Gierer, J. Org. Chem., 41, 3668 (1976). For an analogous dimerization of ortho-lithiated benzoate anion, see W.E. Parham and Y. A. Sayed, J. Chem. Soc., Chem. Commun., 39, 2051 (1974).
46. We gratefully acknowledge the financial support of the Natural Sciences and Engineering Research Council of Canada.