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  Home > JCE Print > Journal of Chemical Education > Issues > 1997  > August  >
Chemical Education Today
Letters
Chemical Magic: An Update (re J. Chem. Educ. 1994, 71, 538)
George B. Kauffman
Cover
August 1997
Vol. 74 No. 8
p. 900
Full Text
Shortly after the publication of the late Ray Seymour's and my "Products of Chemistry" article, "Chemical Magic: Polymers from a Nonexistent Monomer" (J. Chem. Educ. 1994, 71, 538), Thomas T. Tidwell of the Department of Chemistry, University of Toronto, kindly called my attention to a article reporting the preparation and polymerization of vinyl alcohol, the "nonexistent monomer" of our title. Anna K. Cederstav and Bruce M. Novak of the University of California, Berkeley have succeeded in polymerizing almost quantitatively vinyl alcohol (H2C=CHOH), the thermodynamically unstable enolic tautomer of acetaldehyde (H3CCHO), generated in situ by the hydrolysis of a precursor (ketene methyl vinyl acetal) and siphoned off faster than it can tautomerize to acetaldehyde (J. Am. Chem. Soc. 1994, 116, 4073). The first report of hydrolysis conditions that yield metastable vinyl alcohol solutions with a significant lifetime at room temperature makes this previously "nonexistant monomer" a synthetically useful substrate. The two Berkeley chemists are investigating alternative catalyst systems that may allow them to carry out the homopolymerization of vinyl alcohol and other thermodynamically unstable enols.

Thus scientific progress has disproved another of the "factual truths" that many of us learned in school. Time marches on.

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 Kauffman, George B. J. Chem. Educ. 1997 74 900.
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June 23, 2005
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