The Second Centennial Congress Plenary Lecture: Remote Oxidation and Related Reactions Speaker: Ronald Breslow, Columbia University
That evening, after a picnic dinner with entertainment by "The Little German Band," the participants were treated to a lecture on "Remote Oxidation and Related Reactions" by Ronald Breslow of Columbia University. The extremely high selectivity exhibited by enzymecatalyzed reactions has long challenged the organic chemist to devise simpler systems that could exhibit the high selectivity so important for syntheses of complex natural products. Dr. Breslow's group sought high selectivity in steroid syntheses by attaching to substrates a "catalyst" whose reactive site was positioned by a rigid attachment chain of fixed length. Their early successes with remote oxidations were reported in 1969 and 1970. For example, 3-0-cholestanol was selectively functionalized at C-7, -12 and -14, by use of remote photochemical oxidations. In certain systems, "fine tuning" between various positions of attack can be accomplished by solvent changes. A climaxing example was that of the "catcher's mitt" system wherein a selective halogenating group is attached through a rather rigid linkage to one end of a steroid molecule. The reactive portion can then "catch" chlorine atoms from a cheap, externally furnished halogenating agent and then selectively chlorinate certain remote posi-
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tions on the steroid. Dehydrohalogenation has then resulted in high yields of selectively dehydrogenated (overall) molecules in, for example, cortisone-type systems. The "mitt" itself can, of course, be removed a t an appropriate time. The general approach described holds promise as a means of achieving high selectivity in a variety of organic reactions.
Preamble t o "Oxygen Day" A high point of the conference was provided by the brief, but delightful, program presented by R. A. Olofson and J. J. Villafrance of Pennsylvania State University utilizing historical materials associated with previous ceremonies at the Priestley house. As is common with such materials, considered from a distant time, they transmitted both the seriousness of historical moments and the humorous quaintness of some of the proceedings. Included were readings of appropriate poetry and prose, and viewings of photographs of the 1874 centennial celebration and film of a 1926 event a t the Priestley House. All presentations prepared the group for the historic event to occur on the next day.
Oxygen Day Northumberland
The day of the Second Centennial of Chemistrv cererno~ nies began with a busride through the beautiful Penosylvania countryside to the Joseph Priestley House in Northumberland. Ceremonies at the hillside site of Priestley's grave included the now-traditional "Fi!e of the Red Roses" and readings from eulogies of 1874. The group of over 300 then moved to the Priestley House, overlooking the Susquehanna River, for further activities of the day. Among the special events a t the House was the unveiling, by Bernard J. Friedman, President of the American Chemical Society, of a plaque commemorating the origin of the Society. The group meeting a t the First Centennial of Chemistry celebration had appointed a committee which subsequently founded the American Chemical Society in 1876. Thus, the Priestley House is entwined in several important historical threads in chemistry. Another interesting sidelight to the special events was, as in 1874, the
Centennial of Chemistry Awards In recognition of the significance of the events being commemorated on the first of August, 1974, an award was established for presentation a t the Priestley House on that date and a t every subsequent Centennial Celebration. To be known as the Centennial of Chemistry Award, it is sponsored jointly by the American Chemical Society Division of Chemical Education and the Pennsylvania State University Department of Chemistry. "The award honors a scientist for a research contribution in the preceding century which caused a revolution in the teaching of chemistry." Two awards were presented at the ceremonies. Joseph Priestley was designated the recipient of the 1874 First Centennial of Chemistry Award, thus formalizing the mandate of the 1874 convention which dated modern chemistry's birth from the discovery of oxygen, "the most important link in the chain" leading to overthrow of the phlogistic hypothesis. Sir Derek Barton of the Imperial College of Science and Technology, London, was presented the 1974 Second Centennial of Chemistry Award for "putting :he third dimension" into the teaching of organic :hemistry through his contributions to the concept >f conformation. For his development of conforma:ional analysis, Dr. Barton shared the. 1969 Nobel Prize.
appointment of a committee to represent chemists of the United States at a Priestley celebration to be held in Birmingham, England, later this year. To the chagrin of some appointees the representation was to he, as in 1874, "in spirit" only. It is feared by some that this approach might be precedent-setting among universities and foundations. A high point of the ceremonies was the establishment and presentation of Centennial of Chemistry Awards. "The Priestley Heritage: Prospects for Chemistry in Its Third Hundred Years" was presented as the keynote address by Franklin A. Lone: of Cornell Uniuer.sity. Dr. Long viewed the future in a broad sense suggesting that it was conceivable that any similar celebration in 2074 might have to be held in some location other than one of the present major countries if we did not learn better how to use and control our scientific discoveries. International science and technology is well within the purview of Dr. Long in light of his formal contributions to the formulation of national science policy and his efforts on behalf of nuclear arms control. The visit to Northumberland also provided opportunity for the conference participants to tour the Priestley House and Museum. Volume 52, Number 7. January 1975 / 11
