Reactions of lignin model β-aryl ethers with acetyl bromide

Holzforschung

Volumn 50, Issue 4, 1996, Pages 360-364

  Lu, Fachuang ^a,b   Ralph, John ^a,b  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b U S DAIRY FORAGE RESEARCH CENTER   (United States)

Author keywords

Acetyl bromide; Acetylation; Benzyl aryl ether; Bromination; Lignin; Lignin model compound; Aryl ether; Ether; Aryl ether; Ether

Indexed keywords

MODEL COMPOUND; REACTION MECHANISM;

LIGNIN;

EID: 0030356934     PISSN: 00183830     EISSN: None     Source Type: Journal    
DOI: 10.1515/hfsg.1996.50.4.360     Document Type: Article

References (20)

1. Bagby, M.O., R. L. Cunningham and R.L. Maloney. 1973. Ultraviolet spectral determination of lignin. Tappi 56 (4): 162-163.
2. Dence, C. W. 1992. The determination of lignin. In: Methods in lignin chemistry. Eds. S. Y. Lin and C. W. Dence. Springer-Verlag, Heidelberg, pp. 33-61.
3. Iiyama, K. and A. F. A. Wallis. 1988. An improved acetyl bromide procedure for determining lignin in woods and wood pulps. Wood Sci. Technol. 22 (3): 271-280.
4. Iiyama, K. and A. F. A. Wallis. 1989. The effect of acetyl bromide treatment on the ultraviolet spectra of lignin model compounds. Holzforschung 43: 309-316.
5. Iiyama, K. and A. F. A. Wallis. 1990. Dissolution of wood with acetyl bromide solutions - reactions of lignin model compounds. J. Wood Chem. Tech. 10 (1): 39-58.
6. Johansson, B. and G.E. Miksche. 1972. Über die Benzyl-arylätherbindung im Lignin. II. Versuche an Modellen. Acta Chem. Scand. 26 (1): 289-308.
7. Johnson, D.B., W.E. Moore and L.C. Zank. 1961. The spectrophotometric determination of lignin in small wood samples. Tappi 44: 793-789.
8. Lai, Y. and X. Guo. 1992. Acid-catalyzed hydrolysis of aryl ether linkages in wood. Holzforschung 46 (4): 311-314.
9. Landucci, L.L., S.A. Geddes and T.K. Kirk. 1981. Synthesis of carbon-14-labeled 3-methoxy-4-hydroxy-α-(2-methoxyphenoxy)-β-hydroxypropiophenone, a lignin model compound. Holzforschung 35 (2): 67-70.
10. Martin, J. 1967. Determination of lignin in small pulp and paper samples using the acetyl bromide method. Tappi 50: 335-337.
11. Meshgini, M. and K. V. Sarkanen. 1989. Synthesis and kinetics of acid-catalyzed hydrolysis of some α-aryl ether lignin model compounds. Holzforschung 43: 239-243.
12. Morrison, I.M. 1972. Improvements in the acetyl bromide technique to determine lignin and digestibility and its application to legumes. J. Sci. Food Agr. 23 (12): 1463-1469.
13. Nimz, H. 1966. Ätherspaltungen an Lignin-Modellsubstanzen durch Acetolyse. Liebigs Ann. Chem. 691: 126-133.
14. Ralph, J. and R. F. Helm. 1993. The lignin/hydroxycinnamic acid/ polysaccharide complex: Synthetic models for regiochemical characterization. In: Forage Cell Wall Structure and Digestibility. Eds. H. G. Jung, D.R. Buxton, R.D. Hatfield and J. Ralph. ASA-CSSA-SSSA, Madison. pp. 201-246.
15. Ralph, J., R.F. Helm, R.C. Fort and T.J. Elder. 1994a. Stereoselectivity in benzyl 1,2-diaryl ether cleavage by bromotrimethylsilane. J. Chem. Soc., Perkin Trans. 1 (15): 2117-2121.
16. Ralph, J., W.L. Landucci, S.A. Ralph and L.L. Landucci. 1994b. NMR Database of Model Compounds for Lignin and Related Plant Cell Wall Components. Available over the Internet at http://www.dfrc.wisc.edu/software; or send E-Mail tojralph@facstaff.wisc.edu.
17. Ralph, J. and R. A. Young. 1981. Synthesis of the lignin model compounds threo-guaiacylglycerol-β-guaiacyl ether and threoveratrylglycerol-β-guaiacyl ether. Holzforschung 35 (1): 39-41.
18. Ralph, J. and R.A. Young. 1983. Stereochemical aspects of addition reactions involving lignin model quinone methides. J. Wood Chem. Technol. 3 (2): 161-181.
19. Veejendra, K.Y. and G.F. Alex. 1986. Regioselective cleavage of 2-methyltetrahydrofuran: a versatile synthesis of 1-halo-4-pentanols and 4-halo-1-pentanols. J. Org. Chem. 57 (17): 3372-3374.
20. Zawadowski, T. 1968. Reactions of acetyl chloride, bromide, and iodide with hydroxymethyl derivatives of phenol. Rocz. Chem. 42: 297-307.