Letter from Michael Heidelberger to Hugh S. Taylor, Princeton University
Heidelberger had helped to synthesize cyclooctatetraene, the next higher analog of benzene (consisting of a ring with eight
carbon atoms and four double bonds), during a year of postdoctoral study (1911-12) in the laboratory of the 1915 Nobel Laureate,
Richard Willstatter, at the Federal Polytechnic Institute in Zurich, Switzerland. His research with Willstatter on cyclooctatetraene
was controversial, and was questioned as late as the 1940s by Hugh S. Taylor and Charles D. Hurd. Heidelberger, however,
strongly defended his results, as documented in this letter, pointing out that while Taylor and Hurd showed that cyclooctatetraene
resinifies and degrades at high temperatures, he had worked in cold temperatures continuously for 24 hours to synthesize a
colorless liquid that was both stable and reactive. Heidelberger and Willstatter's results stood, and as a consequence
of their work cyclooctatetraene became a widely used intermediate in organic chemistry.
Number of Image Pages:
1 (53,023 Bytes)
1939-11-07 (November 7, 1939)
Taylor, Hugh S.
This item is in the public domain. It may be used without permission.
Medical Subject Headings (MeSH):
The Making of an Immunologist: Heidelberger's Years at the Rockefeller Institute, 1912-1927
Letter from Michael Heidelberger to Hugh S. Taylor, Princeton University (September 9, 1939)
Letter from Hugh S. Taylor, Princeton University to Michael Heidelberger (November 4, 1939)
Letter from Michael Heidelberger to Charles D. Hurd, Northwestern University (November 8, 1939)
Letter from Charles D. Hurd, Northwestern University to Michael Heidelberger (November 29, 1939)
Letter from Richard Willstatter to Michael Heidelberger (March 27, 1940)
Thank you for your letter and the interesting comparisons between the styrene and cyclooctatetraene derivatives. I still
think it quite probable that there may have been some such rearrangement at the high temperatures at which your experiments
were carried out, as well as the early of Willstatter's and Waser's experiments, cyclooctatriene, the next-to-last
stage of unsaturation, was reduced to cyclooctate, which was identified. And in the experiments I carried out this hydrocarbon
was also isolated and its chain length was shown by oxidation, so that the saturated derivative could not have been ethylocyclohexane.
Moreover, in the new Beilstein this hydrocarbon is stated to be a liquid.
Nevertheless the comparisons you adduce are quite startling, but I think they prove only that a re-examination of the whole
question would lead to interesting results, regardless of the outcome.