Professor P. Federlin is thanked for helpful comments and a copy of Ref. [7 b]. The assistance of Annette Allen, Professor Jean-Marie Lehn, and Dr. Valerij Nikolaev is gratefully acknowledged, as is financial support by the Natural Sciences and Engineering Research Council of Canada, the Petroleum Research Fund administered by the American Chemical Society, and a Killam Fellowship from the Canada Council for the Arts.
The First Century of Ketenes (1905–2005): The Birth of a Versatile Family of Reactive Intermediates†
Article first published online: 8 SEP 2005
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 44, Issue 36, pages 5778–5785, September 12, 2005
How to Cite
Tidwell, T. T. (2005), The First Century of Ketenes (1905–2005): The Birth of a Versatile Family of Reactive Intermediates. Angew. Chem. Int. Ed., 44: 5778–5785. doi: 10.1002/anie.200500098
- Issue published online: 8 SEP 2005
- Article first published online: 8 SEP 2005
- 1Many books entitled as dealing with reactive intermediates have appeared between 1956[1a] and 2004:[1b]
- 1aThe Reactive Intermediates of Organic Chemistry, Wiley-Interscience, New York, 1956;,
- 1bReactive Intermediate Chemistry (Eds.: R. A. Moss, M. S. Platz, M. Jones, Jr.), Wiley, Hoboken, NJ, 2004.
- 2bJ. Am. Chem. Soc. 1900, 22, 757–771;,
- 2cChem. Intell. 2000, 44–49, 57;,
- 3bAm. Chem. J. 1901, 25, 54–62;,
- 3cfor a history of carbocation chemistry, see: Carbonium Ions, Vol. 1, (Eds.: G. A. Olah, P. von R. Schleyer), Wiley-Interscience, New York, 1968, pp. 1–75.
- 5dfor an obituary of Eduard Buchner (1860–1917), see: Ber. Dtsch. Chem. Ges. 1917, 50, 1844–1876. Buchner was awarded the Nobel Prize in 1907 for studies of noncellular fermentation, and died in 1917 from wounds sustained in the war while serving in a field hospital. He also devised the ubiquitous Buchner funnel.
- 6Physical Organic Chemistry, Wiley, New York, 1940.,
- 7aStaudinger recounted[8b] that he went to Strassburg in the fall of 1903, but initially worked in the inorganic chemistry department of Kohlschütter;
- 7bfor a history of chemistry in the Alsace, see: Les Sciences en Alsace 1538–1988, Oberlin, Strasbourg, 1989., ,
- 8bFrom Organic Chemistry to Macromolecules, Wiley, New York, 1970.,
- 10cIn 1909, Wedekind succeeded Kohlschütter as professor in the inorganic chemistry department in Strassburg, where Staudinger had originally been associated: Chem. Zeit. 1930, 54, 90;
- 10dfor an obituary notice of Wedekind (1870–1938), see: Ber. Dtsch. Chem. Ges. A 1938, 71, 196–198.
- 11gfor an obituary notice of Wolff (1857–1919), see: Ber. Dtsch. Chem. Ges. A 1929, 62, 145–159; Wolff received his PhD at Strassburg in 1882 for work with Rudolf Fittig, and was Unterrichts-Assistent (teaching assistant) and Privat-Dozent (junior lecturer) there until 1891.
- 12aDie Ketene, Enke, Stuttgart, 1912;,
- 12eChem. Heritage, 1993–1994, 11, 4–6.,
- 13bdue to A. W. Stewart, later professor in Belfast, and supplied by Professor Alwyn Davies, University College, London;
- 13ffor an obituary notice of N. T. M. Wilsmore (1868–1940), see: J. Chem. Soc. 1941, 59–60
- 14aJ. Chem. Soc. 1908, 93, 946–950;, ,
- 15aJ. Am. Chem. Soc. 1923, 45, 515–521;, ,
- 15dC. D. Hurd, Org. Synth. Coll. 1932, 1, 330–334;
- 16aMonatsh. Chem. 1919, 40, 391–402;,
- 16cAsymmetric Organic Reactions, Academic Press, New York, 1971, pp. 276–281, 295, 322, 326;, ,
- 17aThe name bisketenes is used because the alternative diketene is applied to the ketene dimer 20;
- 18aHelv. Chim. Acta 1923, 39, 689–697;, ,
- 19cThis work was contained in the dissertation of Rachel Pal'cik at the Leningrad State University (1969). L. L. Shchukovskaya was a synthetic chemist at the Grebenschikov Institute of Silicate Chemistry in Leningrad (now St. Petersburg, Russia) of the Academy of Sciences of the USSR, and her husband A. N. Lazarev carried out the spectroscopic investigations;
- 19dSilicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000, pp. 485–496;,
- 19eBer. Dtsch. Chem. Ges., 1909, 42, 4098–4818;, ,
- 20gR. A. Minns, Org. Synth. Coll. 1988, 6, 1037–1040 (Ed.: W. E. Noland).
- 23Nobel prize winners who have published work on ketene chemistry include R. B. Woodward, E. J. Corey, R. G. W. Norrish, G. Porter, K. Fukui, G. Olah, R. W. Holley, V. Prelog, O. Diels, H. Staudinger, D. Barton, R. Hoffmann, J. Pople, A. Zewail, G. Natta, R. F. Curl, Jr, L. Ruzicka, J. C. Polanyi, and W. N. Lipscomb.
- 24aKirk-Othmer Encyclopedia of Chemical Technology, Wiley, New York, 1995;, ,