γ-Ketoacid Derivatives

References

• Public Health Service postdoctoral fellow, 1969–1971
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• Fellow of the Consejo Nacional de Investigaciones Cientificas y Técnicas, Argentina, 1970–1972
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• Similar acid treatment oflc, whose preparation from la is detailed in the Experimental Section, yielded 2-ethylidenecyclohexanone [bp 50[ddot] (1.5 Torr);ir (neat) C[dbnd]O 5. 94(s), C[dbnd]C 6.20(s) μml; pmr (CCl4) [stilde]1.72 (d, 3, J = 7.0 Hz, Me), 6.64 (qt, 1, J = 7. 0, 2. 0 Hz, olefinic H) ], indicating the primary product (2c) to have undergone isomerization
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• Wilds , A. L. 1942 . J. Amer, Chem. Soc. , 64 : 1421 For base-catalyzed transformations of α-acetonylcyclohexanone relatives of 2b into cyclopentenones see;A. L. Wilds and W. J. Close, ibid., 68, 83 (1946); A. L. Wilds and J. A. Johnson, Jr., ibid., 68, 86 (1946); A. M. Islam and R. A. Raphael, J. Chem. Soc., 4086 (1952); P. Wieland, K. Heusler, H. Ueberwasser, and A. Wettstein, Helv. Chim. Acta, 41, 74 (1958); W. G. Dauben, J. W. McFarland, and J. B. Rogan, J. Org, Chem., 26, 297 (1961)
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• Kaiser , C. , Burger , A. , Zirngibl , L. , Davis , C. S. and Zirkle , C. L. 1962 . J. Org. Chem. , 27 : 768 The ease of cyclopropane cleavage of the aminoesters is in sharp contrast to the stability of most cyclopropyl amines to acid3 [For exceptions among simple amino-and enamino-cyclopropanes see;C. L. Bumgardner, E. L. Lawton, and J. G. Carver, ibid., 37, 407 (1972); G. Fraenkl and J. W. Cooper, J. Amer. Chem. Soc., 93, 7229 (1971); and for recent work on aminocyclopropanes see M. E. Kuehne and J. C. King, J. Org. Chem., 38, 304 (1973) ]
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• Dissolution of 4 in 10% aqueous hydrochloric acid and immediate extraction with methylene chloride yielded 4 hydrochloride, mp 124–126[ddot]
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