Anionic [1,3] sigmatropic rearrangements of an oxy-cope system incorporated in 8-methylenebicyclo[3.2.1]oct-6-ene and related frameworks

Chemistry Letters

Volumn , Issue 5, 1996, Pages 389-390

  Uyehara, Tadao ^a   Inayama, Toshihiro ^a   Ueno, Masako ^b   Sato, Toshio ^b  

^a UTSUNOMIYA UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030500709     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.389     Document Type: Article

References (20)

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2. b) L. A. Paquette, Angew. Chem., Internat. Ed. Engl., 29, 609 (1990).
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13. All new compounds reported here exhibit satisfactory spectral and analytical and/or HRMS characteristics.
14. 3 powder in THF, see: a) T. Inamoto, N. Takiyama, K. Nakamura, T. Hatajima, and Y. Kamiyama, J. Am. Chem. Soc., 111, 4392 (1989).
15. b) N. Greeves and L. Lyford, Tetrahedron Lett., 33, 4759 (1992).
16. Pinacol-type rearrangement of 1-methoxybicyclo[2.2.2]oct-5-en2-ol via an allyl cation intermediate, see: T. Uyehara, T. Inayama, T. Furuta, T. Kato, Y. Yamamoto, M. Ueno, and T. Sato, Bull. Chem. Soc. Jpn., in press.
17. For an example, 1 H-NMR studies of 9 revealed the presence of NOE (0.6%) between the signals due to one of the exomethylene protons and one of the vinyl methylene protons.
18. L. A. Paquette, S. Liang, and P. Glatsis, Synlett., 1990, 663.
19. Key interactions obtained from NOE difference spectra of 4a are those between the signals due to the 5-endo-proton and the methine proton of the vinyl group (2.2% and 2.4%).
20. A reaction of 4a with KH and 18-crown-6 in THF at room temperature for 30 h gave a mixture of many products and 4a. We found neither 12 nor 15 in the mixture.