The selective reduction of aldehydes using polyethylene glycol-sodium borohydride derivatives as phase transfer reagents

Synthetic Communications

Volumn 27, Issue 12, 1997, Pages 2093-2102

  Blanton, James R ^a  

^a THE CITADEL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; MACROGOL; SODIUM BOROHYDRIDE;

ARTICLE; CATALYSIS; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; PHASE TRANSITION;

EID: 0030982193     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006816     Document Type: Article

References (16)

1. Starks, C.M., Liotta, C.L. and Halpern, M. "Phase Transfer Catalysis," Chapman and Hall, New York, 1994, pp. 1-25.
2. (a) Blanton, J.R. and Kruzska, S. J. Microchemical Journal 1993, 47, 120.;
3. (b) Blanton, J.R. Reactive and Functional Polymers 1996, manuscript in press.
4. (a) Santaniello, E., Ferraboschi, P., Fiecchi, A., Grisenti, P. and Manzocchi, A. Gazzetta Chimica Italiana 1987, 117, 701;
5. (b) Santaniello, E., Ferraboschi, P., Fiecchi, A., Grisenti, P. and Manzocchi, J. Org. Chem. 1987, 52, 671;
6. (c) Santaniello, E., Fiecchi, A., Manzocchi, A. and Ferraboschi, A. J. Org. Chem 1983, 48, 3074.
7. Bianchi, G., Achilli, F. and Gamba, A. J. Chem. Soc. Perkin Trans. 1988, 417.
8. (a) Adjidjonou, K. and Caze, C. Eur. Polym. J. 1994, 30, 395;
9. (b) Adjidjonou, K. and Caze, C. Eur. Polym. J. 1995, 31, 749.
10. When 1 was dissolved in water, it underwent a slow hydrolysis.
11. This was a possiblity that was put forth by Santaniello in reference 3c using stoichiometric data. However, the work was not pursued using spectroscopic data.
12. This phenomenon is probably the reason 1 was less reactive toward ketones than the acyloxyborohydrides reported in the literature.
13. Polymer supported: Tomoi, M. and Ford, W.T. "Polymeric Phase Transfer Catalysts Using Functional Polymers," Sherrington, D.C. and Hodge, P, eds., Wiley and Sons, New York, 1988, pp170-190.
14. It was noted that vigorous stirring led to a gelatinous material that behaved as a poor reducing agent. Analysis of this material was not conclusive except the amount of active hydride was substantially lower.
15. The amount of active hydride was determined using a modification of the technique reported by Morton International for the analysis of borohydrides: "Sodium Borohydride Digest, third ed.,"Morton International, Andover, MA, 1995, pp 48-52. The meq of hydride determined in this manner were divided by the weight of the sample to yield a loading in meq of hydride/g of reagent. All samples gave loadings between 1.1 and 1.4 meq of hydride/g of reagent.
16. 2-O), 2.1 (s, -OH).