Intramolecular cyclopropanation of 7-diazotethered-1,3,5-cycloheptatriene: Preparation and reactions of tricyclo[5.3.0.0.2,10]deca-3,5-dien-9-one

Tetrahedron Letters

Volumn 38, Issue 40, 1997, Pages 6993-6996

  Gu, Henry H ^a   McDaniel, Keith F ^a   McMills, Mark C ^a   Yap, Glenn P A ^b   Rheingold, Arnold L ^b  

^a OHIO UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; POLYCYCLIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030881205     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01672-9     Document Type: Article

References (19)

1. (a) Petrel, T.A.; Stephan, J.M.; McDaniel, K.F.; McMills, M.C.; Rheingold, A.L.; Yap, G.P.A. J. Org. Chem. 1996, 61, 4188.
2. (b) Spencer, K.A.; Gubanich, P.J.; Stack, D.; McMills, M.C.; McDaniel, K.F. manuscript in preparation.
3. See, for example: Comprehensive Organometallic Chemistry II; Abel, E.W.; Stone, P.G.A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1994; Vol 12, Chapters 6.1, 6.3, 8.2, and 9.1.
4. See, for example: Comprehensive Organometallic Chemistry II; Abel, E.W.; Stone, F.G.A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1994; Vol 12, Chapters 5.1 and 5.2.
5. Wong, H.N.C.; Hon, M.-Y.; Tse, C.W.; Yip, Y.C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
6. Doering, W.E.; Ferrier, B.M.; Fossel, E.T.; Hartenstein, J.H.; Jones, Jr., M.; Klumpp, G.; Rubin, R.M.; Saunders, M. Tetrahedron 1967, 23, 3943.
7. A similar approach has been reported for the synthesis of the quaianolides. See Rigby, J.H.; Senanayake, C. J. Am. Chem. Soc. 1987, 109, 3147.
8. See, for example (a) Zutterman, E.; DeWilde, H.; Mijngheer, R.; DeClerq, P.; Vanderwalle, M. Tetrahedron 1979, 35, 2389.
9. (b) Isobe, M.; Iio, H.; Kawai, T.; Goto, T. J. Am. Chem. Soc. 1979, 101, 6076.
10. (c) Taber, D. J. Am. Chem. Soc. 1977, 99, 3513.
11. (d) Kondo, K.; Umemoto, T.; Takahatake, Y.; Tunemoto, D. Tetrahedron Lett.. 1977, 113.
12. 13C NMR, and infrared spectra, and elemental analysis or high resolution mass spectra.
13. Davies, H.M.L.; Houser, J.H.; Thornley, C. J. Org. Chem. 1995, 60, 7529.
14. Please see the Selected Experimental section for the experimental procedure and spectroscopic data for this compound.
15. The author has deposited atomic coordinates for 4 with the Cambridge Crystallographic Data Center. The coordinates can be obtained on request, from the Director, Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2, IEZ, UK.
16. 8a and the ortho phenylthio hydrogens. (equations presented)
17. Divinylcyclopropane rearrangements of related systems have been reported. See for example (a) Vedejs, E.; Wilber, W.R.; Twigg, R. J. Org. Chem. 1977, 42, 401.
18. (b) Vedejs, E.; Shepherd, R.A.; Steiner, P. J. Am. Chem. Soc. 1970, 92, 2158.
19. 4,8]deca-2,5,9-triene (10). The authors report that this reaction proceeds via bicyclo[5.3.0]decatrienyl intermediate D. See Gleiter, R.; Zimmermann, H.; Sander, W.; Hauck, H. J. Org. Chem. 1987, 52, 2644. (equations presented)