HAROLD HART A Personal Appreciation By
G.J. KARABATSOS
Deportment of Chemistry Michigan Stole Uniwrsity
Harold Hart retires this year as Editor of CHEMICAL REVIEWS after a service of ten years. Since there are no signs that his career as an educator and scientist has started losing any of its youthful vigor, this note, although not a prolog, will comprise only a.small portion in the final count of Harold Hart's contributions to chemistry and the chemical profession. It is intended to give a brief overview of his professional contributions up to now and express our pleasure to him for the splendid job that he did as an Editor. Harold Hart was born in New York City on May 14,1922 where he attended elementary school and high school. He began his undergraduate work at Brooklyn College and completed it with highest honors at the University of Illinois (B.S., 1941). The prevailing climate of the times influenced him in going to Pennsylvania State University from where he received the M.S. degree in 1943 and Ph.D. degree in 1947, both under Professor J. H. Simons. Harold Hart began his now distinguished professional career as an instructor of chemistry at Michigan State University in 1946: he was promoted to assistant professor in 1948, to associate professor in 1954, and to professor in 1957. There he became the major motivating force in transforming the department from one whose primary function was to teach chemistry as a service to other departments within the University, to one that is now counted among the excellent departments in the nation. He helped bring this change, as other distinguished scientists have done for their departments in the past, by the force of his strong and persuasive personality, a clear vision of excellence and dedication to it, the establishment of high personal professional standards admired by colleagues, the constant enthusiasm for and involvement in one's chosen profession, and above all the ability to place the creation of a distinguisheddepartment above personal ambitions. His concern for good teaching, so evident in the classroom and so well articulated in the conference room, is further witnessed by his coauthorship of a fine elementary organic chemistry textbook and an equally impressive laboratory manual. As author of more than 175 papers, Harold Hart has made significant contributions in several areas of research. In 1956 he discovered an elegant and now widely used synthesis of dicyclopropyl ketone. He was first to synthesize cyclopropyllithium, tricyclopropylcarbinol, and numerous polycyclopropanes. In 1963, he discovered that peroxytrifluoracetic acid-boron trifluoride was a convenient source of "positive hydroxyl" for direct oxidation of aromatic compounds to phenols. Application of the oxidation to fully substituted aromatics not only led to viable syntheses of previously unaccessible cyclohexadienones (and from the strained nonplanar aromatics such as octamethylnapthalene) but also provided a model for analogous re-
arrangements observed in biological aromatic oxidations (NIH shift). He also has made major contributions to carbonium ion chemistry. For example, he first called attentionto and synthesized multicharged carbocations. Work on protonated bicyclo[3.1.0]hexenones provided the first example of a (1,4)sigmatropic rearrangement, whose stereochemistry was consistent with orbital symmetry conservation. He recently provided the first experimental example of a theoretically predicted novel type of bonding in carbocations, in which one carbon atom is pyramidal and pentacoordinate. In the field of photochemistry, Hart provided the first example of the general oxadi-?r-methane rearrangement. He made the important discovery that the path of photoisomerizations ordinarily performed in solution can be usefully altered by irradiating the same substances after first absorbing them on a polar surface. In recognition of his scientific achievements, Harold Hart has received several awards and honors. Michigan State University honored him in 1965 with the Distinguished Faculty Award and the Michigan State University Chapter of Sigma Xi with its Junior Award in 1960 and its Senior Award in 1972. He received the 1962 American Chemical Society Award in Petroleum Chemistry, was a Margenau Lecturer at Hartwick College in 1968, a Guggenheim Fellow at Harvard in 1955-56, and an NSF Senior Postdoctoral Fellow at Cambridge University in 1962-63. Frequently and with distinction Harold Hart has served the chemical society and his profession in various capacities. Prominent among these have been membership on the Editorial Board of the Journaloforganic Chemistryfrom 1965 to 1970, on the National Science Foundation Chemistry Panel from 1963 to 1965, on the American Chemical Society Petroleum Research Fund Advisory Board from 1966 to 1968, on the Executive Committee of the ACS Organic Section from 1969 to 1972, and on the Program Committee of the ACS Petroleum Division. He has served as a consultant to the New York State Education Department from 1973 to 1974, Editorial Advisor to Houghton Mifflin Company from 1958 to 1972, consultant to Amoco Chemicals Corporation from 1954 to 1974, and coeditor of Advances in A/icyc/ic Chemistry published by Academic Press. He is a member of the Editorial Advisory Board of Accounts o f Chemical Research, and since 1967 has been the Editor of 3A
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Chemical Reviews, 1977, Vol. 77, No. 1
CHEMICAL REVIEWS. Under his editorship, CHEMICAL REVIEWS strengthened its claim as the leading review chemistry journal in the world, in which are published critical reviews of broad interest and timely subjects. For this we are grateful and indebted to him. He retires as Editor of CHEMICAL REVIEWS but will continue to serve the chemical profession as the Chairman-Elect of the Division of Organic Chemistry of the American Chemical Society, in the capacity of professor of chemistry at Michigan State
University, and, hopefuly, in new and challenging positions. To those of us here at Michigan State University he will continue to be not only the outstanding scientist that he is, but also the man who has been able to articulate clearly the position of the humanist, at times as the chairman of the local board of the American Civil Liberties Union, at times as chairman of the AAUP, at times as a member of the Lecture-Concert Series Committee of Michigan State University, but always by the style of his own life.
