Reduction of adamantanone: Face selection induced by 4-Halo and 4,9-Dihalo substitution

Journal of Organic Chemistry

Volumn 61, Issue 12, 1996, Pages 4157-4160

  Kaselj, Mira ^a   Le Noble, William J ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343101792     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9601066     Document Type: Article

References (55)

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26. As in our previous papers, we have for the sake of convenience named all compounds except 12 as numbered in the text. The terms axial (ax) and equatorial (eq) refer to the six-membered ring defined by C-1-5 and C-9.
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34. The only 4,9-substituted adamantanone known is the 4-ax,9-eq-dibromoadamantan-2-one obtained in 4% yield in the reaction of hydrobromic acid with 7-ax-bromo-4-oxohomoadamantan-5-one: Duddeck, H.; Brosch, D. J. Org. Chem. 1985, 50, 5401.
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51. See also: (e) Hrovat, D. A.; Borden, W. T. J. Org. Chem. 1992, 57, 2519. (f) Vinkovic, V.; Mlinaric-Majerski, K.; Marinic, Z. Tetrahedron Lett. 1992, 33, 7441. (b) McKinley, A. J.; Ibrahim, P. N.; Balaji, V.; Michl, J. J. Am. Chem. Soc. 1992, 114, 10631.
52. See also: (e) Hrovat, D. A.; Borden, W. T. J. Org. Chem. 1992, 57, 2519. (f) Vinkovic, V.; Mlinaric-Majerski, K.; Marinic, Z. Tetrahedron Lett. 1992, 33, 7441. (b) McKinley, A. J.; Ibrahim, P. N.; Balaji, V.; Michl, J. J. Am. Chem. Soc. 1992, 114, 10631.
53. See also: (e) Hrovat, D. A.; Borden, W. T. J. Org. Chem. 1992, 57, 2519. (f) Vinkovic, V.; Mlinaric-Majerski, K.; Marinic, Z. Tetrahedron Lett. 1992, 33, 7441. (b) McKinley, A. J.; Ibrahim, P. N.; Balaji, V.; Michl, J. J. Am. Chem. Soc. 1992, 114, 10631.
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55. The author has deposited atomic coordinates for 12 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.