Unusual Variant of the Favorsky Rearrangement. Formation of α-Keto Acetals

Advanced Synthesis and Catalysis

Volumn 339, Issue 4, 1997, Pages 390-393

  Sarhan, Abd El Wareth A O ^a   Hoffmann, H M R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

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EID: 2742580455     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (17)

1. U. Karama, H. M. R. Hoffmann, Chem. Ber. 125 (1992) 2809
2. a) R. J. Giguere, D. I. Rawson, H. M. R. Hoffmann, Synthesis 1978, 902;
3. b) R. J. Giguere, H. M. R. Hoffmann, M. B. Hursthouse, J. Trotter, J. Org. Chem. 46 (1981) 2868;
4. c) H. M. R. Hoffmann, U. Karama, Chem. Ber. 125 (1992) 2803;
5. d) A. A. O. Sarhan, H. M. R. Hoffmann, Chem. Ber. 127 (1994) 1755
6. S. A. Hardinger, C. Bayne, E. Kantorowski, R. McClellan, L. Larres, M.-A. Nuesse, J. Org. Chem. 60 (1995) 1104. The reactive intermediate should be formulated as a metal oxyallyl cation rather than a free, naked oxyallyl species which would not be sufficiently electrophilic for attack of anthracene. See H. M. R. Hoffmann, Angew. Chem., Int. Ed. Engl. 23 (1984) 1
7. S. A. Hardinger, C. Bayne, E. Kantorowski, R. McClellan, L. Larres, M.-A. Nuesse, J. Org. Chem. 60 (1995) 1104. The reactive intermediate should be formulated as a metal oxyallyl cation rather than a free, naked oxyallyl species which would not be sufficiently electrophilic for attack of anthracene. See H. M. R. Hoffmann, Angew. Chem., Int. Ed. Engl. 23 (1984) 1
8. Reviews: J. Mann, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, G. Pattenden, eds., Vol. 3, p. 839, Pergamon Press, Oxford, 1992; A. Baretta, B. Waegell, Reactive Intermediates, R. A. Abramovitch, ed., Vol. 2, p. 527, Plenum Press, New York 1982; P. J. Chenier, J. Chem. Educ. 55 (1978) 286; Y. A. Titov, Russ. Chem. Rev. 39 (1970) 732; A. S. Kende, Org. React. 11 (1960) 261
9. Reviews: J. Mann, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, G. Pattenden, eds., Vol. 3, p. 839, Pergamon Press, Oxford, 1992; A. Baretta, B. Waegell, Reactive Intermediates, R. A. Abramovitch, ed., Vol. 2, p. 527, Plenum Press, New York 1982; P. J. Chenier, J. Chem. Educ. 55 (1978) 286; Y. A. Titov, Russ. Chem. Rev. 39 (1970) 732; A. S. Kende, Org. React. 11 (1960) 261
10. Reviews: J. Mann, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, G. Pattenden, eds., Vol. 3, p. 839, Pergamon Press, Oxford, 1992; A. Baretta, B. Waegell, Reactive Intermediates, R. A. Abramovitch, ed., Vol. 2, p. 527, Plenum Press, New York 1982; P. J. Chenier, J. Chem. Educ. 55 (1978) 286; Y. A. Titov, Russ. Chem. Rev. 39 (1970) 732; A. S. Kende, Org. React. 11 (1960) 261
11. Reviews: J. Mann, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, G. Pattenden, eds., Vol. 3, p. 839, Pergamon Press, Oxford, 1992; A. Baretta, B. Waegell, Reactive Intermediates, R. A. Abramovitch, ed., Vol. 2, p. 527, Plenum Press, New York 1982; P. J. Chenier, J. Chem. Educ. 55 (1978) 286; Y. A. Titov, Russ. Chem. Rev. 39 (1970) 732; A. S. Kende, Org. React. 11 (1960) 261
12. Reviews: J. Mann, Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, G. Pattenden, eds., Vol. 3, p. 839, Pergamon Press, Oxford, 1992; A. Baretta, B. Waegell, Reactive Intermediates, R. A. Abramovitch, ed., Vol. 2, p. 527, Plenum Press, New York 1982; P. J. Chenier, J. Chem. Educ. 55 (1978) 286; Y. A. Titov, Russ. Chem. Rev. 39 (1970) 732; A. S. Kende, Org. React. 11 (1960) 261
13. R. K. Hill, G. R. Newkome, J. Org. Chem. 34 (1969) 740
14. Base-induced cyclization of α,α′-dibromo ketones to cyclopropanones: R. Breslow, J. Posner, Org. Synth. Coll. Vol. V 1973, p. 514; R. Breslow, J. Posner, A. Krebs, J. Am. Chem. Soc. 85 (1963) 234. Ring-contraction to α,β-unsaturated esters: J. Wohllebe, E. W. Garbisch, Jr., Org. Syn. Coll. Vol. VI 1988, 368. Conversion of a bicyclic cyclopropenone into an α-diketone: M. Suda, S. Masamune, J. Chem. Soc., Chem. Commun. 1974, 504
15. Base-induced cyclization of α,α′-dibromo ketones to cyclopropanones: R. Breslow, J. Posner, Org. Synth. Coll. Vol. V 1973, p. 514; R. Breslow, J. Posner, A. Krebs, J. Am. Chem. Soc. 85 (1963) 234. Ring-contraction to α,β-unsaturated esters: J. Wohllebe, E. W. Garbisch, Jr., Org. Syn. Coll. Vol. VI 1988, 368. Conversion of a bicyclic cyclopropenone into an α-diketone: M. Suda, S. Masamune, J. Chem. Soc., Chem. Commun. 1974, 504
16. Base-induced cyclization of α,α′-dibromo ketones to cyclopropanones: R. Breslow, J. Posner, Org. Synth. Coll. Vol. V 1973, p. 514; R. Breslow, J. Posner, A. Krebs, J. Am. Chem. Soc. 85 (1963) 234. Ring-contraction to α,β-unsaturated esters: J. Wohllebe, E. W. Garbisch, Jr., Org. Syn. Coll. Vol. VI 1988, 368. Conversion of a bicyclic cyclopropenone into an α-diketone: M. Suda, S. Masamune, J. Chem. Soc., Chem. Commun. 1974, 504
17. Base-induced cyclization of α,α′-dibromo ketones to cyclopropanones: R. Breslow, J. Posner, Org. Synth. Coll. Vol. V 1973, p. 514; R. Breslow, J. Posner, A. Krebs, J. Am. Chem. Soc. 85 (1963) 234. Ring-contraction to α,β-unsaturated esters: J. Wohllebe, E. W. Garbisch, Jr., Org. Syn. Coll. Vol. VI 1988, 368. Conversion of a bicyclic cyclopropenone into an α-diketone: M. Suda, S. Masamune, J. Chem. Soc., Chem. Commun. 1974, 504