Stereoselective Synthesis of Hydroazulenes from Cyclodecadienols

Journal of the American Chemical Society

Volumn 94, Issue 13, 1972, Pages 4691-4696

  Marshall, James A ^a   Huffman, William F ^a   Ruth, James A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001387666     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00768a042     Document Type: Article

References (43)

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14. A preliminary account of a portion of this work has appeared: J. A. Marshall and W. F. Huffman, J. Amer. Chem. Soc., 92, 6358 (1970).
15. A related system has recently been examined: P. S. Wharton and M. D. Baird, J. Org. Chem., 36, 2932 (1971).
16. Cf. J. B. Hendrickson, Tetrahedron, 7, 82 (1959).
17. Cf. E. D. Brown, M. D. Solomon, J. K. Sutherland, and A. Torre, Chem. Commun., Ill (1967);
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28. For a discussion of allyl cation isomerizations see N. Deno, R. C. Haddon, and E. N. Nowak, J.Amer. Chem. Soc., 92, 6691 (1970);
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35. Cf. J. A. Marshall, C. J. V. Scanio, and W. J. Iburg, J. Org. Chem., 32, 3750 (1967).
36. Cf. “Terpenes and Steroids,” Vol. 1, The Chemical Society, Burlington House, London, 1970, pp 117–119.
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39. N. S. Bhacca and D. H. Williams, “Applications of NMR Spectroscopy in Organic Chemistry,” Holden-Day, San Francisco, Calif., 1966, pp 13–32. Compare chemical-shift values of 18-methyl groups in steroids with 14-α vs. 14-β hydrogens.
40. Cf. P. Kristiansen and T. Ledaal, Tetrahedron Lett., 2817 (1971).
41. Reactions were conducted under a nitrogen atmosphere using the apparatus described by W. S. Johnson and W. P. Schneider (“Organic Syntheses,” Collect. Vol. IV, Wiley, New York, N. Y., 1963, p 132). Reaction products were isolated by addition of water and extraction with the specified solvent. The combined extracts were washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed from the filtered solutions on a rotary evaporator. Short-path distillations were carried out on a Büchi kugelrohrofen using bulb-to-bulb apparatus. Stereochemical designations of substituents in bicyclic compounds are indicated by c (cis) and t (trans) relative to a reference substituent r.
42. E. J. Corey, M. Chaykovsky, and R. Greenwald, J. Org. Chem., 28, 1128 (1963).
43. H. O. House and V. Kramar, J. Org. Chem., 28, 3362 (1963).