The singular reduction of 1,8-bis-hydroxymethylnaphthalene to a benzonorcaradiene by LiAlH4

Tetrahedron Letters

Volumn 38, Issue 47, 1997, Pages 8161-8164

  Popovici Müller, Janeta V ^a   Spencer, Thomas A ^a  

^a Dartmouth College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,8 BIS(HYDROXYMETHYL)NAPHTHALENE; 2,3 BENZONORCARADIENE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

EID: 0342601357     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10247-7     Document Type: Article

References (20)

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4. Trost, B.M. J. Am. Chem. Soc. 1967, 89, 1847-1851.
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6. Kamada, T.; Wasada, N.; Yamamoto, O. Bull. Chem. Soc. Jpn. 1976, 49, 275-282.
7. 4). The signals for the cyclopropane H's in 3 at δ 1.6 and -0.2 ppm have spin-spin splitting patterns essentially identical to those shown for the analogous H's of benzonorcaradiene by Roth, H.D.; Manion Schilling, M.L. Can. J. Chem. 1983, 61, 1027-1035.
8. 4). The signals for the cyclopropane H's in 3 at δ 1.6 and -0.2 ppm have spin-spin splitting patterns essentially identical to those shown for the analogous H's of benzonorcaradiene by Roth, H.D.; Manion Schilling, M.L. Can. J. Chem. 1983, 61, 1027-1035.
9. 4). The signals for the cyclopropane H's in 3 at δ 1.6 and -0.2 ppm have spin-spin splitting patterns essentially identical to those shown for the analogous H's of benzonorcaradiene by Roth, H.D.; Manion Schilling, M.L. Can. J. Chem. 1983, 61, 1027-1035.
10. 4, failed.
11. Jorgenson, M.J.; Friend, A.W. J. Am. Chem. Soc. 1965, 87, 1815-1816.
12. Uyeda, R.T.; Cram, D.J. J. Org. Chem. 1965, 30, 2083-2084.
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14. Snyder, E.I. J. Org. Chem. 1967, 32, 3531-3534.
15. 4 that shows the same solvent dependence, see Franzus, B.; Snyder, E.I. J. Am. Chem. Soc. 1963, 85, 3902-3903.
16. Oi, R.; Sharpless, K.B. Org. Syn. 1996, 73, 1-12; Soai, K.; Oyamada, H.; Takase, M.; Ookawa, A. Bull. Chem. Soc. Jpn. 1984, 57, 1948-1953.
17. Oi, R.; Sharpless, K.B. Org. Syn. 1996, 73, 1-12; Soai, K.; Oyamada, H.; Takase, M.; Ookawa, A. Bull. Chem. Soc. Jpn. 1984, 57, 1948-1953.
18. Kleinfelter, D.C.; Chen, P.H. J. Org. Chem. 1969, 34, 1741-1745.
19. Dreiding models (using S as Al) indicate that either 18 or 19 can readily be manipulated to bring H on "Al" to within 2.0 Å of the receptor C. The distance 2.0 Å was chosen as an appropriate approximation of H-C distance in the transition state on the basis of calculations of the H-C distance in the transition state for addition of LiH to carbonyl groups: Wu, Y.-D.; Tucker, J.A.; Houk, K.N. J. Am. Chem. Soc. 1991, 113, 5018-5027 and Eksterowicz, J.E.; Houk, K.N. Tetrahedron Lett. 1993, 34, 427-430. Semiempirical computations at the AM1 level on 19 and 18 support the conclusion that only a modest increase in energy (10-15 kcal/mol) is required for 19 and 18 to adopt such a geometry. These computations were performed using Spartan, version 4.1, Wavefunction, Inc.: Irvine, CA 92715, 1997. We thank Professor R. Ditchfield for advice concerning these computations.
20. Dreiding models (using S as Al) indicate that either 18 or 19 can readily be manipulated to bring H on "Al" to within 2.0 Å of the receptor C. The distance 2.0 Å was chosen as an appropriate approximation of H-C distance in the transition state on the basis of calculations of the H-C distance in the transition state for addition of LiH to carbonyl groups: Wu, Y.-D.; Tucker, J.A.; Houk, K.N. J. Am. Chem. Soc. 1991, 113, 5018-5027 and Eksterowicz, J.E.; Houk, K.N. Tetrahedron Lett. 1993, 34, 427-430. Semiempirical computations at the AM1 level on 19 and 18 support the conclusion that only a modest increase in energy (10-15 kcal/mol) is required for 19 and 18 to adopt such a geometry. These computations were performed using Spartan, version 4.1, Wavefunction, Inc.: Irvine, CA 92715, 1997. We thank Professor R. Ditchfield for advice concerning these computations.