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THEODORE L. CAIRNS July 20, 1914-September 26, 1994 BY BLAINE C. MCKUSICK THEODORE L. CAIRNS, commonly known as Ted, was a DuPont Company research scientist who macle impor- tant contributions to the science of chemistry, applications of chemistry, en c! U. S. scientific policy. He spent thirty- eight years in DuPont's Central Research Department, the last eight as its director. Cairns was born in Canada in the city of Edmonton, Alberta. He attenclec! Edmonton public schools en c! then enterer! the University of Alberta in 1932 as a chemistry major. He gracluatec! with a B.S. in 1936. He shower! an aptitude for research even as an unclergracluate, co-publish- ing a paper on aminobiphenyls baser! on research clone uncler the direction of Professor Reuben B. Sanclin. About a year before graduation, he met Margaret Jean McDonald, a fellow University of Alberta student majoring in home economics. The scene of their initial meeting a smelly chemistry laboratory-was not especially romantic. His ownership of a rumble-seatec! car, which he hac! pur- chasec! for twenty-five clolIars, perhaps impressed Margaret. They often ciatec! cluring their senior year at the university. Cairns hac! cleciclec! that opportunities for chemists were greater in the Uniter! States than in Canada en c! sought Sanclin's help in gaining admittance to an American graclu 65

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66 BIOGRAPHICAL MEMOIRS ate school. Sanclin recognizec! Cairns's potential as a chem- ist en c! recommenclec! him to the renownec! Professor Roger Aciams of the University of Illinois Chemistry Department. Cairns was acimittec! to that department in the fall of 1936, en c! he promptly starter! to work with Professor Aciams on the stereochemistry of substitutes! biphenyls. The research went well, en c! Cairns receiver! his doctorate in 1939 after only three years, insteac! of the normal four. Academia beckoned, en c! in the fall of 1939, after work- ing that summer in the laboratories of the Eastman Kociak Co., Cairns joiner! the faculty of the Chemistry Department at the University of Rochester as an instructor. Cairns en c! Margaret McDonaTc! hac! not been able to see much of each other after their graduation from the Univer- sity of Alberta (she was working in a Baltimore hospital). However, they corresponded regularly, and they married in Toronto in 1940. Their first chilc! John was born in 1941, by that time Cairns hac! become a U. S. citizen, en c! Margaret follower! suit a year later. Life as a professor seemec! less attractive close up than from a distance, en c! Tecl's former professor, Roger Aciams, Tong a values! consultant to the DuPont Company, painter! a bright picture of research opportunities there. IncleecI, opportunities were very goocI, for Wallace Carothers en c! DuPont colleagues had recently discovered the first practi- cal synthetic fiber (nylon) en c! the first practical synthetic rubber (neoprene). Cairns visitor! the laboratories of the DuPont Experimental Station in Wilmington, Delaware, was favorably impressed by the chemists he met en c! the facili- ties he saw, en c! left the University of Rochester to join DuPont in 1941, a few months before the Uniter! States entered World War II. At the time Cairns came to DuPont, the importance of nylon was well recognized there. It seemed that its chemi

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THEODORE L. CAIRNS 67 Cal mollification might open up new uses for it, en c! Cairns stucliec! its mollification by formalclehycle en c! other reac- tants. Some of the work was instigates! by wartime neecis for nylon with special properties. Interesting, patentable results were obtained. With the coming of peace, expansion of research became possible, en c! the DuPont Experimental Station grew rap- icIly. With the expansion came a new! for strong, capable research leaclers, en c! Cairns soon fount! himself the leacler of a group of eight or so Ph.D. chemists seeking useful applications of chemistry. His group looked for a new chem- istry of cheap, reactive raw materials such as acetylene, eth- yTene, carbon monoxide, hydrogen sulficle, en c! hydrogen cyanide. Thus they turner! up N-methylo! polyamicles by the reaction of formalclehycle with polyamicles. iCO (CH2) 4CONH (CH2) 6NHin CH2O _ > iCO (CH2) 4CO NH (CH2) 6NHin CH2OH In examining the effect of very high pressure on chemi- cals, they fount! that a pressure of 8000 atmospheres con- vertec! nitrites to s-triazines. CH3 N N 3CH3CN-------> a: j~ CHs ~n 3 Such pressures on mixtures of ketones en c! hydrogen sul- ficle proviclec! gem-clithols, previously unknown. R2C=0 + OH'S-------> R2C(SH)2 + H2O Impressed by the properties of poly~tetrafluoroethyTene),

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68 BIOGRAPHICAL MEMOIRS or Teflon, cliscoverec! elsewhere in DuPont, Cairns proposer! the synthesis en c! polymerization of the as yet unknown tetracyanoethylene. Its initial synthesis was not easy, but once that hurcIle was passed, it prover! a very reactive, versatile chemical. Although it failer! as a source of polymers, it former! six-memberec! ring aciclucts with I,3-clienes, four-memberec! ring aciclucts with viny! ethers, brilliantly colorer! tricyanoviny! dyes with aromatic amines, en c! many other classes of procI- ucts. (NC) 2 C=C (CN) 2 + CH2=CHCH=CH2 ----> (NC) 2 C=C (CN) 2 + ROCH=CH2 ----> (NC) 2 C=C (CN) 2 + R2NC6H5 ----> (CN) 2 (CN) 2 ~ ~ (CN)2 RO I '~CN)2 R2N ~C (CN) =C (CN) 2 Tetracyanoethylene readily forms an anion radical, for ex- ample, by reaction with potassium: (NC) 2C=C (CN) 2 + K -----> K+ (NC) 2 C - C (CN) 2 This anion raclical hac! unanticipated! stability, permitting isolation of various of its salts with interesting electronic, optical, en c! magnetic properties. These salts have been the subject of wiclespreac! studies for the past thirty years. The clecamethy~ferrocenium salt was the first molecule-basec! fer- romagnetic material ever characterized. Its critical tempera- ture was only 4.~K, but a salt prepared from dibenzene- vanadium is ferromagnetic above room temperature. An extraordinary variety of magnetic properties is available from the radical anions of TCNE and other cyanocarbons. This

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THEODORE L. CAIRNS 69 subject was reviewoc! in Chemical and Engineering News fairly recently. ~ Cairns was graclually given greater responsibility in DuPont, becoming the laboratory director of the Central Research Department in 1952, its research director in 1966, en c! cli- rector of the entire department in 1971. When the Central Research Department merger! with DuPont's Development Department in 1977, Cairns became director of the result- ant Research en c! Development Department, an organiza- tion of huncirecis of chemists en c! engineers clevotec! to clis- covering new chemistry and developing practical applications for it. Cairns retiree! in 1979, with a multitucle of his co-workers of the preceding thirty-eight years jamming the DuPont Country Club ballroom to demonstrate their friendship en c! admiration for him. He hac! been an inspiring leacler who, as his long-time colleague Robert M. Joyce has pointer! out, "was an inspiring leader with a sharp eye for spotting chemical talent en c! a great sense of putting the right person in the right job." Cairns participates! in many professional activities, espe- cially in the field! of chemical publication. He was on the Eclitorial Boarc! of Organic Syntheses (1949-56) en c! then servec! on its Boarc! of Directors for several years. He subsequently worker! similarly for its sister publication Organic Reactions, serving on its Eclitorial Boarc! from 1960 to 1969. He playoc! a truly vital role for Organic Reactions from 1967 to 1969. Its eclitor-in-chief Arthur Cope suciclenly cliec! in 1967. With great uncertainty as to the publishing plans en c! commit- ments that Cope hac! macle, none of the other editors was willing to take Cope's place. Cairns, unwilling to see this useful publication clie, became its unofficial eclitor-in-chief until William Dauben of the University of California, Ber- keley, with urging from Roger Aciams en c! Cairns, acceptec!

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70 BIOGRAPHICAL MEMOIRS the job in 1969. His acceptance was just in time to see that volume 17 was issues! en c! that this important chemical pub- lication got back on its feet. Cairns remainec! on the Acivi- sory Boarc! of Organic Reactions for several years, cluring which time he co-authorec! an important chapter on "Cy- clopropanes from Unsaturates! Compounds, Methylene Io- clicle, en c! Zinc-Copper Couple."2 Cairns was on the Boarc! of Editors of the Journal of Or- ganic Chemistry from ~ 965 to ~ 970. He was active in the American Chemical Society both locally en c! nationally. He was on the Executive Committee of its Organic Division in 1955-56, its chairman in 1964-65, en c! represented! it on the American Chemical Society Council cluring most of the pe- rioc! 1955-65. He was electec! to the National Academy of Sciences in 1966 after having server! on one of its most important com- mittees, the Committee for the Survey of Chemistry, in 1964- 65. This committee proclucec! a definitive en c! influential assessment of basic research in chemistry in the Uniter! States. His broad experience and knowledge in science and tech- nology was put to use through membership on several im portant government committees: The Delaware Governor's Council on Science and Technology, 1969-72 President Nixon's Science Policy Task Force, 1969 The President's Science Advisory Committee, 1970-73 The President's Committee on the National Medal of Science, 1974-75 The Polytechnic Institute of New York Advisory Council for Chemistry, 1976-78 For several years Cairns chairec! the Division of Chemis- try and Chemical Technology of the National Research Coun- cil. His accomplishments were recognizes! by several awarcis: The City of Wilmington's Outstanding Citizen Award, 1963

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THEODORE L. CAIRNS 71 The American Chemical Society Award for Creative Work in Synthetic Or- ganic Chemistry, 1968 SOCMA (Society of Chemical Manufacturers Association) Medal for Cre- ative Research in Synthetic Organic Chemistry, 1968 Honorary Doctor of Laws degree, University of Alberta, 1970 Perkin Medal, American section of the Society of Chemical Industry, 1973 Cresson Medal, The Franklin Institute, 1974 Cairns wouIc! use the occasion of an aware! to express views on the progress of technology en c! the future of re- search, thereby influencing both. For example, on receiv- ing the Perkin Mecial of the Society of Chemical Industry in New York in 1973, the topic of his aciciress was "The Environment for Inclustrial Research." He notes! the impor- tance of investigation to improve product lines en c! pro- cesses en c! to fins! alternative raw materials to improve quality or Tower mill costs. However, he stresses! the value of searching for new products en c! new ventures to be at the heart of business ten to fifteen years in the future. He concluclec! by saying that "the woric! offers no enc! of clifficult problems to be solver! en c! will be glac! to try whatever solutions we can provicle at a reasonable price." Tec! en c! Margaret Cairns hac! four chiTciren: John A., a Minneapolis lawyer, Margaret Etter, a professor of organic chemistry, crystallography, en c! solic! state interactions at the University of Minnesota, who cliec! in 1992, Elizabeth Reveal, a Washington, D.C., financial aciviser to local gov- ernments, en c! lames R., a manager of trust accounts for a Philaclelphia bank. The family was always close knit. As the chilciren were growing up, the family clic! many things to- gether, such as tennis, skating, gardening, en c! travel. After retirement Cairns continued to follow the course of chemistry en c! other sciences with interest, but he sel- clom playoc! an active role. He occasionally attenclec! scien- tific meetings, such as clinner meetings of the editors of

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72 BIOGRAPHICAL MEMOIRS Organic Syntheses or Organic Reactions, when the meetings happenec! to be nearby. He at last hac! time to pursue his hobby of gardening, especially the raising of unusual variet- ies of dahlias. However, age gradually caught up with him, and on September 26, 1994, he died in Wilmington at age eighty. Besicles his wife en c! three chilciren, Cairns was sur- vivec! by a sister, Eleanor Cairns Everington of Stony Plain, Alberta, eight grancichilciren, en c! three great-grancichilciren. Robert M. Joyce was a close frienc! en c! colleague of Cairns for four decades, beginning in graduate school days at the University of Illinois en c! extending through extensive col- laboration in the DuPont Company. He well described Cairns as "an inspiring leacler with a sharp eye for spotting chemi- cal talent en c! a great sense for putting the right person in the right job."3 NOTES 1. T. S. Miller and A. T. Epstein, "Designer Magnets," Chem. Eng. News 73 (No. 40) (Oct. 2, 1995~: 30-41. 2. Cyclopropanes from unsaturated compounds, methylene io- dide, and zinc-copper couple. Org. React. 20~1973~:1-131. 3. R. M. Joyce. "Theodore L. Cairns," Org. React. 47~1995~:vii . . . vail.

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THEODORE L. CAIRNS SELECTED BIBLIOGRAPHY 1936 With R. B. Sandin. Formation of cyclic azo compounds from 2,2' diaminobiphenyls. 7. Am. Chem. Soc. 58:2019. 1939 With R. Adams. 2-substituted biphenyls. 7. Am. Chem. Soc. 61:2179. 1946 N-methylol polyamides. U. S. Patent 2,393,972. 1947 73 Polyamide/formaldehyde reactions and products thereof. U. S. Patent 2,430,860. N-alkoxymethyl polyamides. U. S. Patent 2,430,908. 1948 Polyamides. U. S. Patent 2,441,057. With R. E. Benson. Chemical reactions of caprolactam. 7. Am. Chem. Soc. 70:2115. 1949 With H. D. Foster, A. W. Larchar, A. K. Schneider, and R. S. Schreiber. Preparation and properties of N-methylol, N-alkoxymethyl, and N-alkylthiomethyl polyamides. 7. Am. Chem. Soc. 71:665. 1950 With A. W. Larchar and B. C. McKusick. High-pressure synthesis of s-triazines. U. S. Patent 2,503,999. With R. E. Benson. Some new reactions of cyclooctatetracne. 7. Am. Chem. Soc. 72:5355. 1951 N-vinylalkyleneureas and polymers thereof. U. S. Patent 2,541,152. 1952 With V. A. Engelhardt, H. L. Jackson, G. H. Kalb, and J. C. Saner. The reaction of acetylene with acrylic compounds. 7. Am. Chem. Soc. 74:5636.

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74 BIOGRAPHICAL MEMOIRS With G. L. Evans, A. W. Larchar, and B. C. McKusick. Gem-dithiols. J. Am. Chem. Soc. 74:3982. With A. W. Larchar and B. C. McKusick. The trimerization of n triles at high pressures. J. Am. Chem. Soc. 74:3633. 1954 With D. D. Coffman, R. Cramer, A. W. Larchar, and B. C. McKusick. Olefin-carbon monoxide-alcohol copolymers. J. Am. Chem. Soc. 76:3024. 1957 With others. Cyanocarbon chemistry: Synthesis and chemistry of tetracyanoethylene. J. Am. Chem. Soc. 79:2340. 1958 With others. Preparation and reactions of tetracyanoethylene.J. Am. Chem. Soc. 80:2775. With B. C. McKusick, R. E. Heckert, D. D. Coffman, and H. F. Mower. Cyanocarbon chemistry. VI. Tricyanovinylamines. J. Am. Chem. Soc. 80:2806. 1960 With C. G. Krespan and B. C. McKusick. Dithietene and bicyclooctatriene ring systems from bis-~fluoroalkyl~acetylenes. J. Am. Chem. Soc. 82:1515. 1961 With C. G. Krespan and B. C. McKusick. Bis-(polyfluoroalkyl~acetylenes. II. Bicyclooctatrienes through 1,4-addition of bis- (polyfluoro~acetylenes to aromatic rings.J. Am. Chem. Soc. 83:3428. With B. C. McKusick. Cyanocarbon chemistry. Angew. Chem. 73:520. 1962 With D. R. Eaton, A. D. Josey, R. E. Benson, and W. D. Phillips. Unpaired electron distribution in pi-systems. J. Am. Chem. Soc. 84:4100. 1963 With B. Graham and H. G. Tanner. Radiation grafting onto pre- swollen polymers. U. S. Patent 3,101,275.

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THEODORE L. CAIRNS 1964 75 With E. G. McGeer. Colored 1:1 pi complexes of tetracyanoethylene and aromatic compounds. U. S. Patent 3,140,308. 1965 With E. Graef. Tetracyanoethylene. U. S. Patent 3,166,584.