Isomerization of Trimethyl α-Keto Trithioorthocarboxylates into α,α-Bis(methylthio) Thiolcarboxylates. A New Rearrangement of Synthetic Interest

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7228-7233

  Degani, Iacopo ^a   Dughera, Stefano ^a   Fochi, Rita ^a   Gazzetto, Sonia ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001419139     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970683+     Document Type: Article

References (22)

1. Barbero, M.; Cadamuro, I.; Degani, I.; Dughera, S.; Fochi, R. J. Org. Chem. 1995, 60, 6017.
2. Degani, I.; Dughera, S.; Fochi, R.; Serra, E. J. Org. Chem. 1996, 61, 9572.
3. Degani, I.; Dughera, S.; Fochi, R. (National Research Council of Italy) Italian Pat. MI96A 000500, 1996; PCT/EP 97/01258 (12.03.1997).
4. For example, see: Hamor, G. H. In Principles of Medicinal Chemistry; Foye, W. O., Ed.; Lea & Febiger: Philadelphia, 1989; Chapter 23 and references cited therein.
5. Degani, I.; Dughera, S.; Fochi, R.; Gatti, A. Synthesis 1996, 467.
6. For example, see: (a) Advances in Linear Free Energy Retationships; Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York, 1972; Chapter 2, and references cited therein, (b) Buckley, A.; Chapman, N. B.; Shorter, J. J. Chem. Soc. B 1969, 195. (c) Chapman, N. B.; Shorter, J.; Utley, J. H. P. J. Chem. Soc. 1962, 1824.
7. For example, see: (a) Advances in Linear Free Energy Retationships; Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York, 1972; Chapter 2, and references cited therein, (b) Buckley, A.; Chapman, N. B.; Shorter, J. J. Chem. Soc. B 1969, 195. (c) Chapman, N. B.; Shorter, J.; Utley, J. H. P. J. Chem. Soc. 1962, 1824.
8. For example, see: (a) Advances in Linear Free Energy Retationships; Chapman, N. B., Shorter, J., Eds.; Plenum Press: New York, 1972; Chapter 2, and references cited therein, (b) Buckley, A.; Chapman, N. B.; Shorter, J. J. Chem. Soc. B 1969, 195. (c) Chapman, N. B.; Shorter, J.; Utley, J. H. P. J. Chem. Soc. 1962, 1824.
9. One reviewer has suggested the following Scheme to formally interpret the reactions carried out in the presence of trityl perchlorate (3) or me thane sulfonic acid (4).
10. + where, according to the scheme, there should be a protonation at the carbonyl group, ab initio calculations, carried out at the MP2/6-31G(d) level and aimed to check this hypothesis, did not provide any conclusive information.
11. Basu, B.; Mukherjee, D. J. Chem. Soc., Chem. Commun. 1984, 105.
12. Dauben, H. J.; Honnen, L. R.; Harmon, K. M. J. Org. Chem. 1960, 25, 1442.
13. Barbero, M.; Cadamuro, I.; Degani, I.; Dughera, S.; Fochi, R. J. Chem. Soc., Perkin Trans. 1 1993, 2075.
14. Froling, A.; Arens, J. F. Red. Trav. Chim. Pays-Bas 1962, 81, 1009.
15. Schmid, M. D.; Bolliger, H. R. Helv. Chim. Acta 1954, 884.
16. Neubert, M. E.; Fishel, D. L. In Organic Synthesis; Freeman, J. P., Ed.; John Wiley & Sons, Inc.: New York, 1990; Collect. Vol. 7, PP 420-423.
17. Sonawane, H. R.; Bellur, N. S.; Kulkarni, D. G.; Ayyangar, N. R. Tetrahedron 1994, 50, 1243.
18. Wladislaw, B.; Marzorati, L.; Biaggio, F. C. J. Org. Chem. 1993, 58, 6132.
19. Bredereck, H.; Gompper, R.; Seiz, H. Chem. Ber. 1957, 90, 1837.
20. Grossert, J. S.; Dubey, P. K. J. Chem. Soc., Chem. Commun. 1982, 1183.
21. Lapkin, I. I.; Rodygin, A. S.; Rybakova, M. N.; Bykova, L. M.; Belonovich, M. I. Zh. Org. Khim. 1977, 13, 996; Chem. Abstr. 1977, 87, 134344.
22. Lapkin, I. I.; Rodygin, A. S.; Rybakova, M. N.; Bykova, L. M.; Belonovich, M. I. Zh. Org. Khim. 1977, 13, 996; Chem. Abstr. 1977, 87, 134344.