Zusammenfassung
Die Autoren stellen fest, daß die 1881 vonMarkownikoff undKrestownikoff synthetisierte Verbindung, die bisher als Cyclobutan-1,3-dicarbonsäure angesehen wurde, tatsächlich 1-Methylcyclopropan-1,2-dicarbonsäure ist.
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References
W. Markownikoff andA. Krestownikoff, Ann.208, 333 (1881).
W. Markownikoff, Ber.23R, 432 (1890).
E. Haworth andW. H. Perkin, jun., J. Chem. Soc.73, 330 (1898). During the last half-century, although the acid has been resynthesized in various connections (F. R. Goss andC. K. Ingold, J. Chem. Soc.127, 2776 (1925).
A. Wassermann, Helv. chim. acta13, 207 (1930).
E. R. Buchman, A. O. Reims, andM. J. Schlatter, J. Amer. Chem. Soc.64, 2703 (1942).
E. R. Buchman et al., unpublished) and the mechanism of its formation has been under discussion5, the assigned structure has never been questioned.
Cf.W. H. Perkin, jun., J. Chem. Soc. 1347 (1929).
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C. K. Ingold, J. Chem. Soc.127, 387 (1925).
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Cf.W. H. Perkin, jun.,loc cit.
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Notably the instability of the acid (cis form) toward hydrochloric acid (E. R. Buchman, A. O. Reims, andM. J. Schlatter,loc. cit., p. 2704); cf. also the behavior of the diamine C4H10N2 and of the dibromide C4H6Br2 obtained from the acid by appropriate degradative techniques (E. R. Buchman et al., unpublished).
Although the ring closure step involves a nucleophilic attack on a tertiary halogen grouping, the steric and other factors are such that the reaction may be expected to proceed smoothly (cf.K. E. Wilzbach, F. R. Mayo, andR. Van Meter,loc. cit., p. 4071). The authors are indebted to Dr.Saul Winstein for a discussion on this point.
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This investigation was carried out under a contract between the Office of Naval Research and the California Institute of Technology.
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Deutsch, D.H., Buchman, E.R. The presumed synthesis of 1,3-cyclobutane-dicarboxylic acid by Markownikoff and Krestownikoff. Experientia 6, 462 (1950). https://doi.org/10.1007/BF02154104
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DOI: https://doi.org/10.1007/BF02154104