Synthesis, reactions, and properties of 2,8-didehydronoradamantane derivatives

European Journal of Organic Chemistry

Volumn , Issue 6, 1999, Pages 1401-1406

  Mlinarić Majerski, Kata ^a   Kragol, Goran ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

2,8 Didehydronoradamantane derivatives; Cyclopropylcarbinyl; Rearrangements; Ring opening reactions

Indexed keywords

ADAMANTANE DERIVATIVE; CYCLOPROPANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ELECTRON TRANSPORT; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 0042107926     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199906)1999:6<1401::AID-EJOC1401>3.0.CO;2-S     Document Type: Article

References (20)

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6. It is known that β,γ-unsaturated ketones could undergo a formal [1,3]-shift of the acyl group to give isomeric β,γ-unsaturated ketones, see: S. S. Hixon, P. S. Mariano, H. E. Zimmerman, Chem. Rev. 1973, 73, 531-551.
7. 4,8]nonan-3-one[7] followed by acid-catalysed rearrangement and oxidation with PCC[2].
8. A. Nickon, H. Kwasnik, T. Swartz, R. O. Williams, J. B. DiGiorgio, J. Am. Chem. Soc. 1965, 87, 1615-1616.
9. Our experimental results are in accordance with a set of bicyclobutonium ion structures[9]. We thank the referee for pointing out that the parent cyclopropylcarbinyl cation has been shown to be a rapidly equilibrating mixture of the classical cyclopropylcarbinyl cation and the bicyclobutonium ion, with both species having almost the same energy, see: M. Saunders, K. E. Laidig, K. B. Wiberg, P. v. R Schleyer, J. Am. Chem. Soc. 1988, 110, 7652-7659; W. Koch, B. Liu, D. J. DeFrees, J. Am. Chem. Soc. 1988, 110, 7325-7328.
10. Our experimental results are in accordance with a set of bicyclobutonium ion structures[9]. We thank the referee for pointing out that the parent cyclopropylcarbinyl cation has been shown to be a rapidly equilibrating mixture of the classical cyclopropylcarbinyl cation and the bicyclobutonium ion, with both species having almost the same energy, see: M. Saunders, K. E. Laidig, K. B. Wiberg, P. v. R Schleyer, J. Am. Chem. Soc. 1988, 110, 7652-7659; W. Koch, B. Liu, D. J. DeFrees, J. Am. Chem. Soc. 1988, 110, 7325-7328.
11. -1, and the final product arises from 13. Under the same conditions both alcohols exo-11 and endo-11 rearrange to give exo-brend-4-en-2-ol (5a). For the chemistry of 11 → 5a see ref.[3]
12. -1.
13. P. Rollin, Synth. Commun. 1986, 16, 611-616.
14. 5 (see Experimental Section).
15. For the photochemically induced electron transfer reactions see: T. Kirschberg, J. Mattay, Tetrahedron Lett. 1994, 39, 7217-7220; B. Pandey, A. T. Rao, P. V. Dalvi, P. Kumar, Tetrahedron 1994, 50, 3843-3848; J. Cossy, N. Furet, Tetrahedron Lett. 1993, 34, 8107-8110.
16. For the photochemically induced electron transfer reactions see: T. Kirschberg, J. Mattay, Tetrahedron Lett. 1994, 39, 7217-7220; B. Pandey, A. T. Rao, P. V. Dalvi, P. Kumar, Tetrahedron 1994, 50, 3843-3848; J. Cossy, N. Furet, Tetrahedron Lett. 1993, 34, 8107-8110.
17. For the photochemically induced electron transfer reactions see: T. Kirschberg, J. Mattay, Tetrahedron Lett. 1994, 39, 7217-7220; B. Pandey, A. T. Rao, P. V. Dalvi, P. Kumar, Tetrahedron 1994, 50, 3843-3848; J. Cossy, N. Furet, Tetrahedron Lett. 1993, 34, 8107-8110.
18. A. Nickon, H. R. Kwasnik, C. T. Mathew, T. D. Swartz, R. O. Williams, J. B. DiGiorgio, J. Org. Chem. 1978, 43, 3904-3916.
19. The identity of 5a, 5b and 11 was established by comparison of their spectral data with the spectra of authentic samples prepared by an alternative route; see ref.[3]
20. 4 takes place from the exo-side to give endo-8 as the major product.