William von Eggers Doering's many research achievements during the first 65 years of his career in chemistry

Accounts of Chemical Research
Frank-Gerrit KlärnerRonald M Magid

Abstract

This Account highlights William von Eggers Doering's important discoveries in many fields of chemistry. His synthetic and mechanistic studies have contributed to areas including non-benzenoid aromatics, carbenes, pericyclic reactions, and diradical intermediates. Doering's synthesis with L. H. Knox of the highly stable tropylium ion and their investigation of its reactivity were the starting point for the development of the field of non-benzenoid aromatics. Working with A. K. Hoffmann, Doering demonstrated the synthesis of dichloro- and dibromocarbene by base-induced alpha elimination of HCl or HBr from CHCl3 or CHBr3 under anhydrous conditions. These results allowed for the synthesis of a variety of cyclopropanes and derivatives including allenes. Using 14C labeling experiments, Doering and Prinzbach showed that the mechanism of insertion of singlet methylene into a C-H bond was a concerted process.In their work on the Cope rearrangement, Doering and Roth's outstanding stereochemical analysis showed that the rearrangement of acyclic 1,5-hexadienes proceeds concertedly, passing over a chairlike transition state. This work has had an enormous impact on the understanding of stereochemical control in synthetic organic chemistry, a...Continue Reading

References

Jan 17, 2002·Journal of the American Chemical Society·John E Baldwin, Edmund J Keliher
Jan 5, 2006·Journal of the American Chemical Society·Charles DoubledayK N Houk
Sep 1, 1981·Proceedings of the National Academy of Sciences of the United States of America·W E Doering
Jul 15, 2006·The Journal of Organic Chemistry·William von E DoeringEckhart K G Schmidt

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Citations

Feb 19, 2015·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Jeffrey I Seeman
Feb 21, 2013·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Jeffrey I Seeman
Feb 12, 2019·Angewandte Chemie·Caroline ApelMathias Christmann
Mar 8, 2014·Beilstein Journal of Organic Chemistry·Sebastian Krüger, Tanja Gaich
Mar 16, 2011·Angewandte Chemie·Frank-Gerrit Klärner
Mar 31, 2021·Chemistry : a European Journal·Jan Maier, Todd B Marder
Oct 8, 2011·The Journal of Organic Chemistry·Aida AjazRichard P Johnson
Nov 5, 2013·The Journal of Organic Chemistry·Alicia C VoukidesRichard P Johnson
Dec 4, 2012·The Journal of Organic Chemistry·Sarah L Skraba, Richard P Johnson

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