Facile synthesis of 2-nitroalkanols by tetramethylguanidine (TMG)-catalyzed addition of primary nitroalkanes to aldehydes and alicyclic ketones

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2749-2752

  Simoni, Daniele ^a   Invidiata, Francesco Paolo ^a   Manfredini, Stefano ^b   Ferroni, Roberto ^b   Lampronti, Ilaria ^b   Roberti, Marinella ^c   Pollini, Gian Piero ^b  

^a UNIVERSITY OF PALERMO   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

^c Dipto di Scienze Farmaceutiche   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; CYCLOALKANOL DERIVATIVE; NITRO DERIVATIVE; NITROALKANE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0030907429     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00461-9     Document Type: Article

References (16)

1. Seebach, D.; Colvin, E W.; Leher, F.; Weller, T. Chimia. 1979, 33, 1.
2. Schickh, O.v.; Apel, G.; Padeken, H.-G.; Schawarz, H. H.; Segnitz, A. in: Houben-Weyl, Methoden der Organischem Chemie, 4th Edn., E. Muller, Ed., Vol. X/1, Georg Thieme Verlag, Stuttgart, 1971.
3. Coombes, R. G.in: Comprehensive Organic Chemistry. Barton, D. H. R.; Ollis, W. D.; Eds., Vol. 2, Pergamon Press, Oxford, 1979.
4. Grundmann, C.; Grunanger, P. in: The nitrile Oxides, Springer Verlag, Heidelberg, 1971.
5. Mikite, G.; Jakucs, E.; Kis-Tamas, A.; Darvas, F.; Lopata, A. Pestic. Sci. 1982, 13, 557.
6. Henry, L. C. R. Acad. Sci. Paris. 1895, 120, 1265.
7. Baer, H. H.; Urbas, L. The Chemistry of the Nitro and Nitroso Groups; Feuer, H. Eds.; Interscience: New York, Vol. 2, 1970.
8. Kabalka, G. W.; Vanna, R. S. Org. Prep. Proc. Int. 1987, 19, 283.
9. Rosini G. In Comprehensive Organic Synthesis, Part 2; Addition to C-X π-Bonds; Trost, B.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 2, 329.
10. Rosini, G.; Ballini, R.; Sorrenti, P. Synthesis. 1983, 1014.
11. Wollemberg, R. H.; Miller, S. J. Tetrahedron Lett. 1978, 35, 3219.
12. Pollini, G.P.; Barco, A.; DeGiuli, G. Synthesis. 1972, 44.
13. Hewson, A. T.; MacPherson, D.T. Tetrahedron Lett. 1983, 24, 647.
14. 4 and after removing the solvent the pure 2-nitroalkanol was obtained by distillation or by flash chromatography.
15. Lambert, A.; Lowe, A. J. Chem. Soc., Perkin Trans 1 1947, 1517, and references cited therein.
16. Dauben, Jr., H. J.; Ringold, H. J.; Wade, R. H.; Pearson, D. L,; Anderson, Jr, A. G. Org. Synth., Coll., 1963, 4, 221.