Substituted triethylene glycols from dibutylstannylene acetals

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 433-436

  Godjoian, Gayane ^a   Wang, Vivian R ^a   Ayala, Alfredo M ^a   Martínez, Ruben V ^a   Martínez Bernhardt, Rolande ^a   Gutiérrez, Carlos G ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIOXANE DERIVATIVE; ALKANEDIOL DERIVATIVE; ETHER DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030051888     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02211-2     Document Type: Article

References (30)

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12. Shanzer, A.; Mayer Shochet, N. J. Chem. Soc. Chem. Commun. 1980, 176; Shanzer, A.; Mayer-Shochet, N.; Frolow, F.; Rabinovich, J. J. Org. Chem. 1981, 46, 4662; Fadda, A.M.; Maccioni, A.M.; Maccioni, E.; Podda, G. Farmaco, 1992, 47, 99; Mandolini, L.; Montaudo, G.; Scamporrino, E.; Roelens, S.; Vitalini, D. Macromolecules, 1989, 22, 3275.
13. Shanzer, A.; Mayer Shochet, N. J. Chem. Soc. Chem. Commun. 1980, 176; Shanzer, A.; Mayer-Shochet, N.; Frolow, F.; Rabinovich, J. J. Org. Chem. 1981, 46, 4662; Fadda, A.M.; Maccioni, A.M.; Maccioni, E.; Podda, G. Farmaco, 1992, 47, 99; Mandolini, L.; Montaudo, G.; Scamporrino, E.; Roelens, S.; Vitalini, D. Macromolecules, 1989, 22, 3275.
14. Shanzer, A.; Mayer Shochet, N. J. Chem. Soc. Chem. Commun. 1980, 176; Shanzer, A.; Mayer-Shochet, N.; Frolow, F.; Rabinovich, J. J. Org. Chem. 1981, 46, 4662; Fadda, A.M.; Maccioni, A.M.; Maccioni, E.; Podda, G. Farmaco, 1992, 47, 99; Mandolini, L.; Montaudo, G.; Scamporrino, E.; Roelens, S.; Vitalini, D. Macromolecules, 1989, 22, 3275.
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18. For comparison with the organotin methodology presented here, the reaction of the potassium or sodium alkoxide of diol 3a with dibromoethane resulted largely in elimination products.
19. Tor, Y.; Libman, J.; Shanzer, A.; Lifson, S. J. Am. Chem. Soc. 1987, 109, 6517.
20. The reported melting point for the meso isomer is 124-126 ° (C. Considine J. Organometallic Chem, 1966, 5, 263). We have found that the melting point of the racemic modification is 141-142°C.
21. a) The formation of dioxane from the reaction of dibromoethane and the stannylene acetal derived from ethylene glycol has been previously observed: Pommier, J.-C.; Valade, J. C. R. Acad. Sc. (Paris) 1965, 4549;
22. b) The formation of 2,3-dimethyl-1,4-dioxane has been reported from ethylene glycol bis(tributylstannyl) ether and dibromoethane: Ratier, M.; Delmond, B.; Pommier. J.-C. Bull. Soc. Chim. Fr. 1972, 1593.
23. Castro, P.P.; Tihomirov, S.; Gutierrez J. Org. Chem. 1988, 53, 5179.
24. For examples of internal alkylation of haloalkyltributyltinalkoxides to form oxygen heterocycles: Delmond, B.; Pommier, J.-C.; Valade, J. J. Organometallic. Chem. 1972, 35, 91; Odeh, A.M.S.; Usta, J.A.; Issidorides, C.H. Heterocycles 1980, 189.
25. For examples of internal alkylation of haloalkyltributyltinalkoxides to form oxygen heterocycles: Delmond, B.; Pommier, J.-C.; Valade, J. J. Organometallic. Chem. 1972, 35, 91; Odeh, A.M.S.; Usta, J.A.; Issidorides, C.H. Heterocycles 1980, 189.
26. The diacylation of stannylene acetals is also stepwise: Shanzer, A.; Libman, J.; Gottlieb, H.; Frolow, F. J. Am Chem. Soc. 1982, 47 4220; Morcuende, A.; Valverde, S.; Herradon, B. Synlett. 1994, 89; Helm, R.F.; Ralph, J.; Anderson, L. J. Org. Chem. 1991, 56, 7015; Reginato, G.; Ricci, A.; Roelens, S.; Scapecchi, S. J. Org. Chem. 1990, 55, 5132.
27. The diacylation of stannylene acetals is also stepwise: Shanzer, A.; Libman, J.; Gottlieb, H.; Frolow, F. J. Am Chem. Soc. 1982, 47 4220; Morcuende, A.; Valverde, S.; Herradon, B. Synlett. 1994, 89; Helm, R.F.; Ralph, J.; Anderson, L. J. Org. Chem. 1991, 56, 7015; Reginato, G.; Ricci, A.; Roelens, S.; Scapecchi, S. J. Org. Chem. 1990, 55, 5132.
28. The diacylation of stannylene acetals is also stepwise: Shanzer, A.; Libman, J.; Gottlieb, H.; Frolow, F. J. Am Chem. Soc. 1982, 47 4220; Morcuende, A.; Valverde, S.; Herradon, B. Synlett. 1994, 89; Helm, R.F.; Ralph, J.; Anderson, L. J. Org. Chem. 1991, 56, 7015; Reginato, G.; Ricci, A.; Roelens, S.; Scapecchi, S. J. Org. Chem. 1990, 55, 5132.
29. The diacylation of stannylene acetals is also stepwise: Shanzer, A.; Libman, J.; Gottlieb, H.; Frolow, F. J. Am Chem. Soc. 1982, 47 4220; Morcuende, A.; Valverde, S.; Herradon, B. Synlett. 1994, 89; Helm, R.F.; Ralph, J.; Anderson, L. J. Org. Chem. 1991, 56, 7015; Reginato, G.; Ricci, A.; Roelens, S.; Scapecchi, S. J. Org. Chem. 1990, 55, 5132.
30. Dialkylation of the stannylene acetal of 2,2-dimethyl-1,3-propanediol with a bromoacetamide at toluene reflux has been reported: Shanzer, A.; Samuel, D.; Korenstein, R. J. Am. Chem. Soc. 1983, 105, 3815.