Chloromethyl(dimethyl)sulfonium Trifluoromethanesulfonate - The Reagent for Preparation of Acetals of 2-Hydroxyaldehydes from Ketones under Basic Conditions

Synlett

Volumn 1997, Issue 8, 1997, Pages 921-922

  Kaczmarczyk, Grzegorz ^a   Jończyk, Andrzej ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

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Indexed keywords

EID: 1542677238     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-939     Document Type: Article

References (18)

1. Griesbaum, K.; Lie G. O.; Keul H. J. Org. Chem. 1984, 49, 679.
2. Kirrmann, A.; Duhamel, P.; Nouri-Bimorhki, R. Liebigs Ann. Chem. 1966, 691, 33. Kirrmann, A.; Nouri-Bimorhki, R. Bull. Soc. Chim. France 1968, 3213. McDonald, R. N. In Mechanisms of Molecular Migration; Thyagarajan, B. S, Ed.; Wiley: New York, 1971; vol. 3, p. 67.
3. Kirrmann, A.; Duhamel, P.; Nouri-Bimorhki, R. Liebigs Ann. Chem. 1966, 691, 33. Kirrmann, A.; Nouri-Bimorhki, R. Bull. Soc. Chim. France 1968, 3213. McDonald, R. N. In Mechanisms of Molecular Migration; Thyagarajan, B. S, Ed.; Wiley: New York, 1971; vol. 3, p. 67.
4. Kirrmann, A.; Duhamel, P.; Nouri-Bimorhki, R. Liebigs Ann. Chem. 1966, 691, 33. Kirrmann, A.; Nouri-Bimorhki, R. Bull. Soc. Chim. France 1968, 3213. McDonald, R. N. In Mechanisms of Molecular Migration; Thyagarajan, B. S, Ed.; Wiley: New York, 1971; vol. 3, p. 67.
5. Alternatively, 2-hydroxyaldehyde dimethylacetals are prepared by reaction of the corresponding aldehydes with thianthrenium tetrafluoroborate followed by treatment of the initially formed 2-sulfoniumaldehydes with sodium methoxide in methanol: Schulz, M.; Kluge, R.; Michaelis, J. Synlett 1994, 669.
6. Bordwell, F. G.; Pitt, B. M. J. Am. Chem. Soc. 1955, 77, 572.
7. +).
8. The dimethyl acetals or ketals of these carbonyls were main products.
9. 4: C, 69.55; H. 7.30. Found: C, 69.50; H, 7.29.
10. Klabunde, K. J.; Burton, D. J. J. Am. Chem. Soc. 1972, 94, 5985 and references cited therein.
11. 11 are regioselectively deprotonated at methylene benzyl group by alkali metal hydroxides.
12. Hatch, M. J. J. Org. Chem. 1969, 34, 2133.
13. Borredon, M. E.; Delmas, M.; Gaset, A. Tetrahedron 1987, 43, 3945.
14. 2: C, 23.43; H, 4.33. Found: C, 23.30; H, 4.29.
15. Modena, G.; Scorrano, G. J. Chem. Soc., Perkin Trans 2 1979, 1.
16. 16
17. Lampman, G. M.; Koops, R. W.; Olden, C. C. J. Chem.Educ. 1985, 62, 267.
18. Buncel, E. Carbanions: Mechanistic and Isotopic Aspects; Monograph 9 in a series: Reaction Mechanisms in Organic Chemistry; Eaborn, C.; Chapman, N. B., Eds.; Elsevier: Amsterdam, Oxford, New York, 1975, p. 51.