A Biographical Compendium of Organic Name Reactions Rachael K. Dieringer (Faculty Mentor: David E. Lewis) Department of , University of Wisconsin-Eau Claire, Eau Claire, WI 54702, U.S.A.

Arthur Michael: the Student Arthur Michael: the Professor Arthur Michael: the Reaction Education Before College Return to the United States In 1887 Michael published the first of four papers with the title, “Ueber die Addition von Natriumacetessig- und Natriummalonsaüreäthern zu den Aethern ungesättiger Säuren.” In this first report of what is now Michael returned to the United States in 1880, with considerable experi- his eponymous reaction, Michael reported the addition of diethyl so- • Born in Buffalo, New York, to a well-off ence, but no formal degree. Even so, just has he had first been appoint- real estate investor. diomalonate and ethyl sodioacetatoacetate to ethyl cinnamate. Over ed to Hofmann’s group without having satisfied all the requirements, he the course of the next seven years, Michael and his students extend- • Educated at the Classical School in was appointed as an assistant in the chemical at Tufts Col- Buffalo ed the reaction to a wide range of conjugated esters, including acety- lege for a year before being appointed Professor of Chemistry there. He lenic esters • Received instruction in chemistry at was awarded the A. M. from Tufts in 1882, and the Ph.D. in 1890. the Classical School. • His father allowed him to set up a home laboratory and conduct his own ex- perimemnts there. • In his late teens he contracted “brain fever,” most probably scarlet fever. Arthur Michael (1853-1942) • He was not able to enroll at Harvard.

College Education in Europe Tufts College, 1910

In 1871, Michael was admitted to Berlin University, where he studied in August Wilhelm von Hofmann’s laboratory—despite not having the re- In 1889, Michael married his student, Hel- quired chemistry background. After a year in Hofmann’s laboratory, Mi- en Cecilia DeSilver Abbott (1857-1904), an chael continued his studies under at Heidelberg, where organic chemist herself, and one of the few he strengthened his practical training. Two years later, he rejoined Hof- women in the field. In addition, she was fully mann at Berlin and continued his work there from 1875 to 1878. Michael’s intellectual equal. After their mar- riage, the couple spent 18 months traveling Future Directions around the world. Michael was an enthusias- tic mountaineer, and climbed several alpine

Helen Abbott Michael peaks, including the Matterhorn. Arthur Michael (1853-1942): The Michael Addition Reaction We have been invited to sub- The Michael reaction accepted the position of Head of the Chemical Laboratory at is now 130 years old,[1] Clark University in Worcester, Mass—a position he had and its use has continued originally declined. After just one year at Clark, Michael moved (1857-1904) [2] mit a sample article (at left) unabated since. As is so to the Isle of Wight, where he set up a private laboratory. He often the case, the chemist worked in this laboratory for three years. He resumed his behind the reaction is not professorship at Tufts in 1894, and held this position until his nearly as well known to retirement in 1907. Following his retirement, Michael set up a to the online journal, SYN- chemists as the reaction new private laboratory near Boston. In 1912, he was appointed itself. Despite several Professor, without lecturing duties, at Harvard University. He useful biographies of retired from this position in 1936. Michael,[3] most organic In 1887 Michael published the first of four papers with the FORM, for consideration as chemists have little title, "Ueber die Addition von Natriumacetessig- und After their return to the U.S., Michael accepted the position of Head knowledge of his far- Natriummalonsaüreäthern zu den Aethern ungesättiger Säuren." Arthur Michael (1853-1942) reaching work, or of the In this first report of what is now his eponymous reaction, a quarterly feature in the his- razor-sharp intellect that Michael reported the addition of diethyl sodiomalonate and he used to great effect in criticizing the science of his ethyl sodioacetatoacetate to ethyl cinnamate. Over the course of of the Chemical Laboratory at Clark University in Worcester, Mass— contemporaries. the next seven years, Michael and his students extended the Michael was born in Buffalo, New York, and attended reaction to a wide range of conjugated esters, including tory of organic chemistry. classical school there, where he received private instruction in acetylenic esters.[1(d)] chemistry. His father, a well off real-estate investor, encouraged his son's early love for chemistry, setting up a home laboratory a position he had originally declined. After just one year at Clark, Mi- EtO2C CO2Et CO2Et for him and allowing him to conduct his own experiments there. Na + Ph However, toward the end of his teens he suffered a serious EtO2C Ph CO2Et illness (brain fever, possibly scarlet fever), which eliminated his EtO C chael moved to the Isle of Wight, where he set up a private laboratory. chances of entering Harvard College and allowed him to dabble 2 in art and literature before returning to chemistry. August Wilhelm von Hofmann Robert Wilhelm Eberhard Bunsen MeOC CO Et CO2Et In 1871, he was admitted to Berlin University, where he 2 Na + Ph studied in August Wilhelm von Hofmann’s laboratory—despite About SYNFORM He worked in this laboratory for three years. He resumed his profes- EtO2C Ph CO2Et not having the required chemistry background. After a year in Hofmann’s laboratory, Michael continued his studies under MeOC SYNFORM complements the information provided by Robert Bunsen at Heidelberg, where he strengthened his J. prakt. Chem. [2] 1887, 35, 349–356 the Thieme Chemistry E-Journals. It serves the sorship at Tufts in 1894, and held this position until his retirement in practical training. Two years later, he rejoined Hofmann at international chemistry community by publishing . In 1879, Michael conducted research in with Charles-Adolphe Berlin and continued his work there from 1875 to 1878. In 1879, Much of the recent research on the Michael reaction has timely information about: Michael conducted research in Paris with Charles-Adolphe been focused on to extending it to an enantioelective form, especially using chiral organocatalysts. Wurtz, as well as in St. Petersburg with Mendeleev. • new scientific advances in organic chemistry 1907. Following his retirement, Michael set up a new private labora- Michael returned to the United States in 1880, with Wurtz, as well as in St. Petersburg with Mendeleev. considerable experience, but no formal degree. Even so, just has and related fields of research he had first been appointed to Hofmann's group without having Michael’s primary focus was organic theory, in which he • facts and people from the world of chemical satisfied all the requirements, he was appointed as an assistant developed many theories about the forces involved in chemical sciences tory near Boston. In 1912, he was appointed Professor, without lectur- in the chemical laboratory at Tufts College for a year before phenomena. One of his most important contributions was as a being appointed Professor of Chemistry there. He was awarded critic of others’ scientific work. He was renowned as a very • highlights from international chemistry the A. M. from Tufts in 1882, and the Ph.D. in 1890. intuitive critic, frequently being known for pulling no punches. conferences ing duties, at Harvard University. He retired from this position in 1936. In 1889, Michael married his student, Helen Cecilia He stepped on more than a few toes throughout his career as a DeSilver Abbott (1857-1904), scientific critic, being an extensive critic he was hard for others The content of SYNFORM is presented in a stimulating an organic chemist herself, and to ignore. When chemists , Wilhelm Lossen, and thought-provoking manner and features two one of the few women in the Adolph Claus, and Rudolph Fittig raised questions about the sections: The Inside Story and SynStories. field. In addition, she was fully first edition of van’t Hoff’s theory the critiques were brushed Michael's intellectual equal. off and paid almost no mind. This included Kolbe’s infamous In The Inside Story an eminent competent personality After their marriage, the rant on the utter ludicrously of tetrahedral carbons. However, interviews the main author of a recent couple spent 18 months when Michael released his criticisms they took them seriously groundbreaking article, an opinion leader in the traveling around the world. and couldn’t easily refute such an extensive, multi-part critique. Michael was an enthusiastic First refusing to accept Van’t Hoff’s theory of geometrical chemical sciences, or an expert in an important area mountaineer, and climbed isomerism when it first started to gain traction, considering it dealing with chemistry (politics, ethical issues, several alpine peaks, including unjustified and calling the hypothesis unjustified. He proved he society, etc.). the Matterhorn. After their was correct through a series of elaborate experiments, thereby return to the U.S., Michael strengthening the original theory by correcting its mistakes

Acknowledgments

Charles-Adolphe Wurtz Dmitrii Ivanovich Mendeleev We are happy to acknowledge the financial support of the University of Clark University, 1900 Wisconsin-Eau Claire Office of Research and Sponsored Programs