Synthesis and ring-opening reaction of novel 1,3-dehydroadamantanes possessing phenyl and alkoxyl substituents

Tetrahedron

Volumn 69, Issue 15, 2013, Pages 3238-3248

  Inomata, Sotaro ^a   Harada, Yusuke ^a   Matsuoka, Shin Ichi ^a   Ishizone, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

1,3 Dehydroadamantanes; 1,3 Dibromoadamantanes; 1 Acetoxyadamantanes; 1 Methoxyadamantanes; 5 Methoxy 1,3 dehydroadamantane; 5 Phenyl 1,3 dehydroadamantane; Ring opening reaction

Indexed keywords

ACETIC ACID; ADAMANTANE DERIVATIVE; CARBON; CYCLOPROPANE; LITHIUM; METHANOL; PHENYL GROUP;

ACIDITY; ARTICLE; BROMINATION; CARBON NUCLEAR MAGNETIC RESONANCE; ELECTRON; PRIORITY JOURNAL; RING OPENING; SYNTHESIS;

EID: 84875226007     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.02.042     Document Type: Article

References (42)

1. R.E. Pincock, and E.J. Torupka J. Am. Chem. Soc. 91 1969 4593
2. R.E. Pincock, W.B. Scott, and E.J. Torupka Can. J. Chem. 50 1972 3958 3964
3. P. Warner, R. LaRose, and T. Schleis Tetrahedron Lett. 15 1974 1409 1412
4. -1)
5. P.G. Gassman, R.N. Steppel, and E.A. Armour Tetrahedron Lett. 14 1973 3287 3290
6. K.B. Wiberg, W.F. Bailey, and M.E. Jason J. Org. Chem. 41 1976 2711 2714
7. K.B. Wiberg Acc. Chem. Res. 17 1984 379 386
8. K.B. Wiberg Chem. Rev. 89 1989 975 983
9. K.B. Wiberg, and F.H. Walker J. Am. Chem. Soc. 104 1982 5239 5240
10. P.E. Eaton, and G.H. Temme III J. Am. Chem. Soc. 95 1973 7508 7510
11. K.B. Wiberg, H.A. Connon, and W.E. Pratt J. Am. Chem. Soc. 101 1979 6970 6972
12. T. Ishizone, S. Matsuoka, S. Sakai, W. Harada, and H. Tajima Macromolecules 37 2004 7069 7071
13. S. Matsuoka, N. Ogiwara, Y. Uehara, and T. Ishizone Macromol. Symp. 240 2006 206 212
14. S. Inomata, S. Matsuoka, S. Sakai, H. Tajima, and T. Ishizone Macromolecules 45 2012 4184 4195
15. S. Matsuoka, N. Ogiwara, and T. Ishizone J. Am. Chem. Soc. 128 2006 8708 8709
16. R.E. Pincock, and F.-N. Fung Tetrahedron Lett. 21 1980 19 22
17. W.B. Scott, and R.E. Pincock J. Am. Chem. Soc. 95 1973 2040 2041
18. C.S. Gibbons, and J. Trotter Can. J. Chem. 51 1973 87 91
19. W. Adcock, and C.I. Clark J. Org. Chem. 58 1993 7341 7349
20. M. Ohno, K. Shimizu, K. Ishizaki, T. Sasaki, and S. Eguchi J. Org. Chem. 53 1988 729 733
21. S. Kobayashi, T. Matsuzawa, S. Matsuoka, H. Tajima, and T. Ishizone Macromolecules 39 2006 5979 5986
22. S. Kobayashi, H. Kataoka, T. Ishizone, T. Kato, T. Ono, S. Kobukata, and H. Ogi Macromolecules 41 2008 5502 5508
23. D.N. Kevill, K.C. Kolwyck, and F.L. Weitl J. Am. Chem. Soc. 92 1970 7300 7306
24. G.S. Poindexter, and P.J. Kropp J. Org. Chem. 41 1976 1215 1218
25. R.I. Davidson, and P.I. Kropp J. Org. Chem. 47 1982 1904 1909
26. R.A. Moss, J. Tian, and R.R. Sauers Org. Lett. 6 2004 4293 4296
27. I. Ledneczki, and Molnár Á Synth. Commun. 34 2004 3683 3690
28. P.R. Schreiner, O. Lauenstein, I.V. Kolomitsyn, S. Nadi, and A.A. Fokin Angew. Chem., Int. Ed. 37 1998 1895 1897
29. A.A. Fokin, and P.R. Schreiner Adv. Synth. Catal. 345 2003 1035 1052
30. P.R. Schreiner, O. Lauenstein, E.D. Butova, P.A. Gunchenko, I.V. Kolomitsin, A. Wittkopp, G. Feder, and A.A. Fokin Chem. - Eur. J. 7 2001 4996 5003
31. It should be noted that considerable amounts (∼15%) of tribromides of 1-phenyl- and 1-alkoxyadamantanes, such as 1,3,5-tribromo-7-phenyladamantane, 1,3,5-tribromo-7-methoxyadamantane, and 1,3,5-tribromo-7-butoxyadamantane certainly formed in the reaction mixtures using mono-substituted adamantanes, such as 8a, 9a, and 9c after the prolonged reaction (See Supplementary data).
32. 2. After workup, 11b could be isolated in 21% yield.
33. In several cases, trace amounts of corresponding adamantanes were obtained along with the desired DHAs probably due to the reduction of 1,3-dibromoadamantanes with lithium metal.
34. P. Schleyer, R. von, R.C. Fort Jr., W.E. Watts, M.B. Comisarow, and G.A. Olah J. Am. Chem. Soc. 86 1964 4195 4197
35. G.A. Olah, G.K.S. Prakash, J.G. Shin, V.V. Krishnamurthy, G.D. Mateescu, G. Liang, G. Sipos, V. Buss, T.M. Gund, P. Schleyer, and R. von J. Am. Chem. Soc. 107 1985 2764 2772
36. K. Takeuchi, T. Okazaki, T. Kitagawa, T. Ushino, K. Ueda, and T. Endo J. Org. Chem. 66 2001 2034 2043
37. R.M. Jarret, and L. Cusumano Tetrahedron Lett. 31 1990 171 174
38. K. Frei, and H.J. Bernstein J. Chem. Phys. 38 1963 1216 1227
39. P.E. Eaton Angew. Chem., Int. Ed. Engl. 31 1992 1421 1436
40. V.J. Jasys, F. Lombardo, T.A. Appleton, J. Bordner, M. Ziliox, and R.A. Volkmann J. Am. Chem. Soc. 122 2000 466 473
41. P.R. Schreiner, A.A. Fokin, Lauenstein, Y. Okamoto, T. Wakita, C. Rinderspacher, G.H. Robinson, J.K. Vohs, and C.F. Campana J. Am. Chem. Soc. 124 2002 13348 13349
42. Ref. 2. The simultaneous introduction of two different substituents on adamantyl framework was also attained to form 1-bromo-3-ethoxyadamantane by the reaction of 1a in the presence of bromine in diethyl ether. The reaction of 1a with bromine gave a 3-bromo-1-adamantyl cation, and the cation reacted with nucleophilic diethyl ether to provide an oxonium salt. The following elimination of oxonium salt afforded 1-bromo-3-ethoxyadamantane as a major product from 1a.