A New Selective Carbonyl Blocking Group. The Regioselective Protection of p-Quinones

Journal of the American Chemical Society

Volumn 95, Issue 17, 1973, Pages 5822-5823

  Evans, D A ^a   Hoffman, J M ^a   Truesdale, L K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000812802     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00798a095     Document Type: Letter

References (21)

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2. L. H. Sarett, G. I. Poos, J. M. Robinson, R. E. Beyler, J. M. Vandergrift, and G. E. Arth, J. Amer. Chem. Soc., 74, 1393 (1952);
3. R. B. Woodward, F. Sondheimer, D. Taub, K. Heusler, and W. M. McLamore, J. Amer. Chem. Soc., 74, 4223 (1952);
4. R. B. Woodward, F. E. Bader, H. Bickel, A. J. Frey, and R. W. Kierstead, Tetrahedron, 2, 1 (1958).
5. For representative reactions of quinones with organometallic reagents see W. Ried in “Newer Methods of Preparative Organic Chemistry,” Vol. IV, W. Foerst, Ed., Academic Press, New York, N. Y., 1968, pp 97-110;
6. E. Bamberger and L. Blangey, Justus Liebigs Ann. Chem., 384, 272 (1911);
7. H. M. Crawford, J. Amer. Chem. Soc., 57, 2000 (1935);
8. H. M. Crawford and M. McDonald, J. Amer. Chem. Soc., 71, 2681 (1949);
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10. L. S. Hegedus, E. L. Waterman, and J. Catiin, J. Amer. Chem. Soc., 94, 7155 (1972).
11. The reaction of TMSCN with a variety of aldehydes and ketones has been shown by us and others to be a general, high yield transformation: D. A. Evans, L. K. Truesdale, and G. L. Carroll, J. Chem. Soc., Chem. Commun., 55 (1973);
12. W. Lidy and W. Sundermeyer, Chem. Ber., 106, 587 (1973).
13. Prepared according to the procedure of E. C. Evers, W. O. Frei-tag, J. N. Keith, W. A. Kriner, A. G. MacDiarmid, and S. Sujishi, J. Amer. Chem. Soc., 81, 4493 (1959). A more convenient synthesis is being developed in our laboratory.
14. M. Lovnasmaa, Suom. Kemistilehti A, 41, 91 (1968). For example, the structure of 2f may be established by transformation to 5f (R = CH3) whose structure is unequivocal.
15. The KCN-crown complex was prepared by the dissolution of equimolar amounts of KCN and crown ether [R. N. Green, Tetrahedron Lett., 1793 (1972)] in anhydrous methanol. Removal of solvent in vacuo afforded the active catalyst. Tetra-n-butylammonium cyanide is equally effective.
16. For an excellent review of methods of preparation of p-quinols as well as their reactions see A. J. Waring, Adoan. Alicycl. Chem., 1, 129 (1966).
17. Compound 7 has been synthesized independently: L. Fieser and C. Bradsher, J. Amer. Chem. Soc., 61, 417 (1939). This transformation correlates with the structural assignments for both 5j (R = CHs) and 2j.
18. S. Woodwin and B. Witkop, J. Amer. Chem. Soc., 79, 179 (1957);
19. Y. Abe, Bull. Chem. Soc.Jap., 18, 93 (1943).
20. Camille and Henry Dreyfus Teacher-Scholar Recipient (1971-1976);
21. Alfred P. Sloan Fellow (1972-1974).