Chemistry and technology of 2‐alkenyl azlactones
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In this highlight “azlactone” is used as the name for this heterocycle. Nomenclature varies considerably in the literature. For most of our publications we chose to use “azlactone” that dates back to the early 20th century and the original Erlenmeyer–Plochl azlactone and amino acid synthesis that is widely familiar to both organic chemists and biochemists. Chemical abstracts use the more IUPAC acceptable “5(4H)‐oxazolone.” An additional liberty taken with regard to nomenclature is that given the relative importance of the group at position‐2 in determining the chemistry the usual procedure of alphabetically listing all groups has also been abandoned and the group at position‐2 is listed first.
Rasmussen J. K., 1988, Encyclopedia of Polymer Science & Engineering, 558
4‐Alkylidene and 4‐arylidene substituted azlactones have been reported. We have not investigated these derivatives primarily as the result of an earlier report [ref. 4(c)] that indicated their inability to polymerize.
(a) Br Patent 1 121 418 filed June 30 1967 and issued July 24 1968toRohm and Haas GmbH details of which were later published byHubner K.;Kollinsky F.;Markert G.;Pennewiss H.Angew Makromol Chem 1970 11 109;
Over the course of conducting many vacuum distillations and unlike any other monomers in the authors' experience distilled fractions of 2‐alkenyl azlactones often polymerize slowly within a few days of the distillation. This can be prevented by the incorporation of anhydrous sodium carbonate (1 wt %) and 2 6‐di‐t‐butyl‐4‐methylphenol (1000 ppm) in the distillation vessel along with (and importantly) an air bleed into the liquid being distilled.
Pearson R. G., 1967, Chem Br, 103
Heilmann S. M.;Moren D. M.;Rasmussen J. K.;Krepski L. R.U.S. Patent 4 149 806 1992and 5 268 473 1993.
Rasmussen J. K., 1989, New Polymers Based on Azlactone Chemistry. Frontiers of Macromolecular Science, 137
Odian G., 1981, Principles of Polymerization, 433
The computations were conducted by D. K. Misemer and his many contributions are acknowledged.
Heilmann S. M.;Moren D. M.;Rasmussen J. K.;Krepski L. R.;Pathre S. V.U.S. Patent 5 081 197 1992and 5 091 489 1992.
Berger K. C., 1989, Propagation and Termination Constants in Free Radical Polymerization. Polymer Handbook, II67
Babu G. N., 1997, Polym Prepr (Am Chem Soc Div Polym Chem), 38, 510
Kohler M.;Ohngemach J.;Poetsch E.U.S. Patent 4 922 004 1990.
Rasmussen J. K., 1990, Polym Prepr (Am Chem Soc Div Polym Chem), 31, 442
Rasmussen J. K., 1991, React Polym, 199
Rasmussen J. K., 1991, Polym Prepr (Am Chem Soc Div Polym Chem), 32, 426
Similar topographies were obtained using a precipitation polymerization procedure with no particle stabilizer but the resulting supports were more difficult to physically handle because they were particularly susceptible to static electricity effects.
Xie S., 1997, Polym Prepr (Am Chem Soc Div Polym Chem), 38, 211
Tang Y. M.U.S. Patent 4 842 739 1989.
(a)Heilmann S. M.;Drtina G. J.;Eitzman P. D.;Haddad L. C.;Hyde F. W.;Johnson T. W.U.S. Patent 5 478 466 1995;
(b)Heilmann S. M.;Drtina G. J.;Eitzman P. D.;Haddad L. C.;Hyde F. W.;Johnson T. W.;Rasmussen J. K.;Williams M. G.U.S. Patent 5 468 847 1995.
Francis C. J., 1984, J Chem Soc Chem Commun, 579
Krepski L. R.;Heilmann S. M.;Moren D. M.;Rasmussen J. K.U.S. Patent 5 157 108 1992.