Letter from Hugh S. Taylor, Princeton University to Michael Heidelberger
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, pointing out that Taylor and Hurd showed that while 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:
2 (106,320 Bytes)
1939-11-04 (November 4, 1939)
Taylor, Hugh S.
Reproduced with permission of Elizabeth C. Healy.
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 Michael Heidelberger to Hugh S. Taylor, Princeton University (November 7, 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)
There is a remarkable similarity of properties between those reported for cyclo-octa-tetraene and the known properties of
styrene. It was my understanding that a number of organic chemists wonder whether the products obtained by Willstatter and
his co-workers really did represent the properties of cyclo-octatetraene. It was my understanding also that the late Professor
Kohler spent a considerable amount of time and energy in attempting to obtain cyclo-octatetraene. This suggested to me that
he himself was somewhat uncertain that the material previously obtained actually represented the compound sought. I am listing
on the enclosed sheet some of the data of the two compounds which suggested the possible identity of the two. The only property
which seems to deviate in my view is that on page 519 of your reprint: "The spectrum of the hydrocarbon shows no absorption
bands but continuous absorption in the violet beginning at _ = 462 mm at 5 mm. and 490 mm at 30 mm. thickness of layer."
I wonder if these absorption spectra were made in the liquid system. If so they cannot be very convincing and what one really
ought to do is to examine the absorption spectrum in the vapor phase.