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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 7, 1977 - Issue 6
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Original Articles

7-Dimethylvinylidene-1-methoxybicyclo[4.1.0]heptane and Ethyl 1-Ethoxy-2-methylcyclopropane-3-carboxylate

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Pages 375-382 | Received 23 May 1977, Published online: 23 Oct 2006

References

  • Wenkert , E. , Goodwin , T. E. and Ranu , B. C. J. Org. Chem. , in press; E. Wenkert, M. E. Alonso, B. L. Buckwalter, and K. J. Chou, J. Am. Chem. Soc., in press.
  • Wenkert , E. , Mueller , R. A. , Reardon , E. J. Jr. , Sathe , S. S. , Scharf , D. J. and Tosi , G. 1970 . J. Am. Chem. Soc. , 92 : 7428 E. Wenkert, C. A. McPherson, E. L. Sanchez, and R. L. Webb, Synth. Comm., 3, 255 (1973); E. Wenkert, B. L. Buckwalter, and S. S. Sathe, Synth. Comm., 3, 261 (1973).
  • Hartzler , H. D. 1959 . J. Am. Chem. Soc. , 81 : 2024 For a related reaction with cyclohexene see.
  • Sasaki , T. , Eguchi , S. , Ohno , M. and Nakata , F. 1976 . J. Org. Chem. , 41 : 2408 The same type of reaction on other enol ethers was reported by after completion of the present work (K. J. Chou, Ph.D. dissertation, Indiana University, 1975).
  • The shifts are in ppm downfield from TMS {δ(TMS) = δ(CDCl3) + 76.9 ppm} and the starred values may be reversed. The 13C NMR spectra of a deuteriochloroform solution were recorded on a Varian XL-100–15 spectrometer operating at 25.2 MHz in the Fourier transform mode.
  • Crandall , J. K. , Paulson , D. R. and Bunnell , C. A. 1968 . Tetrahedron Lett. , : 5063 Cf. inter alia;M. L. Poutsma and P. A. Ibarbia, J. Am. Chem. Soc., 93, 440 (1971).
  • Early quenching of the hydrolysis of 1 gave indications of the presence of an isopropyl-bearing compound {1H NMR (CCl4) δ 0.97 (d, 6, J = 6 Hz, Me2)} among the products.
  • Komendantov , M. I. , Smirnova , T. S. and Dyakonov , I. A. 1966 . Zh. Org. Khim , 2 : 559 Cf.;3, 1903 (1967) and earlier papers.
  • Salomon , R. G. and Kochi , J. K. 1973 . J. Am. Chem. Soc. , 95 : 3300

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