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Margareta Avram (1920–1984): a Life Dedicated to Organic Chemistry

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Margareta Avram (1920–1984): a Life Dedicated to Organic Chemistry ACADEMIA ROMÂNĂ Rev. Roum. Chim., Revue Roumaine de Chimie 2020, 65(1), 5-22 DOI:10.33224/rrch.2020.65.1.01 http://web.icf.ro/rrch/ Motto: “ Cyclobutadiene, (CH)4, is the Mona Lisa of organic chemistry…” D. Cram (1991, Nobel Price 1987). MARGARETA AVRAM (1920–1984): A LIFE DEDICATED TO ORGANIC CHEMISTRY * Mircea D. GHEORGHIU Department of Chemistry, One Washington Square, San Jose State University, San Jose, CA 95192-0101, USA Received June 1, 2019 The objective of the present paper is to outline the contribution of Prof. Avram to Organic Chemistry, to point out that her pioneering work in the field of cyclobutadiene, benzocyclobutadiene, Friedel-Crafts reactions, polycyclic hydrocarbons and derivatives and Pd(II) organochemistry are, together with contributions of a few international chemists, chemical seeds that proved over time (+50 years) to deliver an abundant intellectual crop that enlarged the area of research and provided a better definition of the scope. Starting a high stake professional life in the aftermath of the devastating second World War (WWII) was an improbable event. In 1940’ in all aspects of life, everything was in scarcity. In chemistry, shortages of chemical documentation (journals, books), unavailability of chemicals, poor equipped and limited lab 1 space associated with instrumentation shortage was common condition. * Corresponding author: [email protected]; Prof. Margareta Avram supervised both the author’s undergraduate Diploma Work and the PhD thesis, Polytechnic Institute, Bucharest, Romania. 6 Mircea D. Gheorghiu Astoundingly, although these shortages, the Laboratory of Organic Chemistry of Polytechnic Institute of Bucharest, founded by Prof. Costin D. Nenitzescu, a German-educated chemist, was an island of delivering highly competitive chemistry. In this intellectual and material environment, the young talented chemist Margareta Avram defended on July 15, 1947 her Thesis “Syntheses in class of 10,11- Benzofluoranthrene” in front of a highly exigent commission: C.D. Nenitzescu, P. Spacu, and E. Georgeacopol. The topics studied in the Thesis are nicely endorsing the life-time interest of Prof. Nenitzescu in the chemistry of hydrocarbons and AlCl3 catalyzed reaction. The research topics were triggered by the confusing chemistry regarding the dimerization of dialin (1,2-dihydronaphthalene) produced by the Brönsted acid, H2SO4 and of tetralin (1,2,3,4- tetrahydronaphthalene) by the Lewis acid AlCl3. 1 In 1921, von Braun and Kirschbaum reported that dialin in presence of H2SO4 produces the hydrocarbon o C20H20 (m.p. 93 C) predicted to contain as structural subunit a four-membered ring. Avram in the Thesis and in the subsequent paper published2 provided an unambiguous support that the correct structure for compound having the m.p. 93 oC is 1 (Scheme 1), without any four-membered ring. Fig. 1 – The cover and the second page of the PhD thesis. 3 o In 1941, Dansi and Ferri described the action of AlCl3 on tetralin at 30-80 C to produce the o hydrocarbon C20H20, m.p. 150.5 C, that afterwards subjected to dehydrogenation gave a hydrocarbon C20H12 with a m.p. 165 oC. M. Avram failed to reproduce the chemistry claimed by the Italian authors. Moreover, when M. Avram have treated tetralin with AlCl3 under various conditions, confirmed the results obtained by G. Schroeter4 who identified as reaction products octahydroanthracene and octahydrophenanthrene. In the PhD Thesis and the published paper is shown eloquently that the intermediates (C20H20) and the dehydrogenated aromatic final product (C20H12) does not contain a cyclobutane ring. Instead, the structures of the intermediates are 1 and 2 (Scheme 1), and the aromatic compound resulted by dehydrogenation is benzo[j]fluoranthene (BjF). Scheme 1 Margareta Avram: a life dedicated to organic chemistry 7 While structure of hydrocarbon 2 was firmly established, for the structure of hydrocarbon with m.p. 93oC, Nenitzescu-Avram opted, with reservation, that probably is 5,6,7,8,9,12,13,14-octahydrobenzofluoranthrene 1 (Scheme 1). The hesitation, a testimony of a distinguished professional ethics, was confirmed after 30 years, when the correct structure including stereochemistry details established by X-ray analysis (see Scheme 1)5 concluded that hydrocarbon 1 and hydrocarbon 2 are diastereoisomers. The structure of the low melting point (93 oC) hydrocarbon resulted in kinetic control is (±)1a (Scheme 1) while the high melting point hydrocarbon (150.5 oC) resulted in thermodynamic control, has the structure of (±)2a. Additionally, six independent syntheses strongly support its aromatic structure shown in Scheme 1 as BjF. The paper resulted from the PhD Thesis was submitted and accepted in 1948 to be published in the Journal of the American Chemical Society (JACS): Fig. 2 – An excerpt from JACS. Fig. 3 – The chemical genealogy of Prof. Avram. Unique for JACS, the paper was printed two years later, namely in August 1950, “because of difficulty of communication.” Next, I would like to add a few comments concerning the professional trajectory at the Polytechnic Institute, Bucharest, Roumania and the Institute of Organic Chemistry, Bucharest, Roumania. 8 Mircea D. Gheorghiu Prof. Avram was a dedicated academic having been a Professor at Bucharest Polytechnic and research scientist at “Costin D. Nenitzescu” Institute of Organic Chemistry from Bucharest. She was brilliant, far-sighted, and scientifically inquisitive. Prof. Avram academic carrier, according to the official “Polytechnic Institute-pages from history (1948– 1992),” presently published on web2 as well, started in 1950 as Instructor, (“asistent,” first level for Professorship in Roumania), then in 1955 she was promoted to Assistant Professor, and in 1968 to Full Professor. In order to facilitate the teaching of Organic Chemistry, she authored a textbook of Organic Chemistry (1983) in two volumes (vol.1 560 p; vol 2. 631 p). Additionally, Prof. Avram authored with Prof. Gh. Mateescu the first and only book in Roumania concerning “Infrared Spectroscopy. Application in Organic Chemistry” (in Roumanian, English, French). Since its inception in 1949, Prof. Avram was also working with what is presently known as Roumanian Academy’s “Costin D. Nenitzescu” Institute of Organic Chemistry, where she was until her death the director of a research group in hydrocarbon chemistry. The professional genealogy of all of us, who had been part of Prof. Nenitzescu’s Organic Chemistry Chair of Polytechnic Institute of Bucharest, is remarkable. It comprises giants of Organic Chemistry: Kekulé, von Bayer, Emil Fischer, Hans Fischer and Costin D. Nenitzescu. Prof. Avram is one of those whose teaching and research achievements has honored her privileged forebears. Prof. Avram’s contributions to Organic Chemistry Now, it is appropriate to resume the chemistry contribution of Prof. Avram. After the JACS publication, Prof. Avram was occasionally involved for a short time in errand topics. The most prominent is the discovery of the mechanism of activation of AlCl3 by water for catalytic isomerization of saturated hydrocarbons. Traces of alkyl halide is also an active cocatalyst.6 In 1957, Prof. M. Avram started an extensive life-time investigation in the (i) Chemistry of Cyclobutane derivatives (61 papers), covering the cyclobutadiene (CBD), Benzo-CBD and related hydrocarbons with four membered ring. The scientific interest in the following years has been diversified to (ii) Reaction of acetylenes with transition metals (11 papers), (iii) Friedel-Crafts acylation of acetylenes (5 papers), (iv) Chemistry of transition-metal organic compounds (2 papers) (v) ketenes (3 papers) and, (vi) miscellaneous topics (40 papers). A. Cyclobutanes and related derivatives The favorite area of research of M. Avram was the chemistry of cyclobutane derivatives. The most read papers are those dedicated to CBD and Benzo-CBD. For example, the paper dealing with CBD dimer has 83 citations: Benzocyclobutadiene paper has 57 citations: and the linear dimer of benzocylobutadiene has 59 citations: A1. Cyclobutadiene (CBD) Cyclobutadiene (C4H4), is a very simple organic molecule that captured the interest of generation of organic chemist for more than a century. One of the longest running sagas of organic chemistry was the attempted preparation of CBD, a molecule with a deceptively simple structure, nevertheless, for many years proved more Margareta Avram: a life dedicated to organic chemistry 9 difficult to access it than to conquer the Mount Everest itself. Cyclobutadiene is not a resonance stabilized molecule, on contrary has highly localized double bonds, and consists of a valence tautomeric equilibrium between two rectangular singlet ground state structures.7–92 Starting in 1957, defying intrinsic difficulties, Nenitzescu and M. Avram have set mapping strategies of CBD synthesis. Their pioneering papers provided convincing proofs that indeed, the elusive CBD10–17 and benzo-CBD18,19 were “freely” involved in the trapping experiments. About the same time, in Germany, R. Criegee was specifically interested in tetramethyl-CBD,20–15 and G. Maier in the parent CBD26-30, and in USA and Canada, S. Masamune31 was appealed in the parent CBD and M. P. Cava32–34 in Benzo-CBD. Unfortunately, none of the above efforts has been finalized successfully, neither the parent CBD nor substituted CBD and neither the parent or substituted Benzo-CBD have been isolated. The relevance of these failures was captured in a superb intellectual analogy by Donald Cram (Nobel Prize in
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