Stereochemistry of Opening of Cyclopropanols. trans-2,3-Di-tert-butylcyclopropanone Hemiketals

Journal of Organic Chemistry

Volumn 37, Issue 12, 1972, Pages 1899-1902

  Whaeton, P S ^a   Fhitzbeeg, A R ^a  

^a WESLEYAN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009517692     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00977a011     Document Type: Article

References (23)

1. Earlier results with discussion are presented by C. H. DePuy, Accounts Chem. Res., 1, 33 (1968), and.
2. T. D. Hoffman and D. J. Cram, J. Amer. Chem. Soc, 91, 1009 (1969).
3. C. H. DePuy, F. W. Breitbeil, and K. R. DeBruin, J. Amer. Chem. Soc, 88, 3347 (1966).
4. A. R. Fritzberg, Ph. D. Thesis, Wesleyan University, 1971.
5. P. S. Wharton and T. I. Bair, J. Org. Chem., 31, 2480 (1966).
6. D. J. Cram, “Fundamentals of Carbanion Chemistry,” Academic Press, New York, N. Y., 1965, Chapters 3 and 4. A useful summary is presented on pp 153–155.
7. A. Nickon, J. L. Lambert, S. J. Lambert, R. O. Williams, and N. H. Werstiuck, J. Amer. Chem. Soc, 88, 3354 (1966).
8. J. F. Pazos and F. D. Greene, J. Amer. Chem. Soc, 89, 1030 (1967).
9. A. S. Kende, Org. React. 11, 261 (1960).
10. L. C. King and G. K. Ostrum, J. Org. Chem., 29, 3459 (1964).
11. For examples of exchange in the Favorskii reaction see F. G. Bordwell, R. R. Frame, R. G. Scamehorn, J. G. Strong, and S. Meyerson, J. Amer. Chem. Soc, 89, 6704 (1967).
12. A. J. Klunder and B. Zwanenburg, Tetrahedron Lett., 1721 (1971).
13. W. T. Borden, V. V. M. Cabell, and T. Ravindranathan, J. Amer. Chem. Soc, 93, 3800 (1971).
14. E. C. Leonard, J. Org. Chem., 30, 3258 (1965).
15. M. L. Oftedahl, J. W. Baker, and M. W. Dietrich, J. Org. Chem., 30, 296 (1965).
16. L. C. Rinzema, J. Stoffelsma, and J. F. Arens, Reel. Trav. Chim. Pays-Bas, 78, 359 (1959).
17. Melting points reported for 1: Leonard, 93-95°; Oftedahl, 96-97°; Rinzema, et al., 92-93°.
18. Neither Leonard's nor Oftedahl's paper presented ir data. However, the ir spectrum of the compound Oftedahl reported as 3 can be found in “Sadtler's Standard Spectra,” Sadtler Research Laboratories, Philadelphia, Pa., 1966, ir spectrum no. 28346.
19. W. E. Truce and J. A. Simms, J. Amer. Chem. Soc, 78, 2756 (1956).
20. J. M. Stirling, J. Chem. Soc., 5856 (1964).
21. Prepared by the m-chloroperbenzoic acid oxidation of the previously reported ethyl phenylethynyl sulfide.
22. L. Brandsma, E. Wijers, and C. Jonkers, Reel. Trav. Chim. Pays-Bas, 83, 208 (1964).
23. Compound 5 has recently been synthesized by an alternate procedure: W. E. Truce and G. C. Wolf, J. Org. Chem., 36, 1727 (1971).