Thioketones – Knowledge and References

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Analytical Chemistry

Published in W. M. Haynes, David R. Lide, Thomas J. Bruno, CRC Handbook of Chemistry and Physics, 2016

W. M. Haynes, David R. Lide, Thomas J. Bruno

1. Willard, H. H., Merritt, Jr., L. L., Dean, J. A., and Settle, F. A., Instrumental Methods of Analysis, 7th Edition, Wadsworth Publishing Co., Belmont, CA, 1988. Chromophore Ether Thioether Amine Amide Thiol Disulfide Bromide Iodide Nitrile Acetylide (alkyne) Sulfone Oxime Azido Alkene Ketone Thioketone Esters Aldehyde Carboxyl Sulfoxide Nitro Nitrite Azo Nitroso Nitrate Conjugated hydrocarbon Conjugated hydrocarbon Conjugated hydrocarbon Conjugated hydrocarbon Conjugated hydrocarbon Conjugated hydrocarbon Conjugated system Conjugated system Conjugated system Phenyl Functional Group -O- -S- -NH2- -CONH2 -SH -S-S- -Br -I

Silylated thiocarbonyl S-methanides as key intermediates in one-pot olefination reactions leading to ferrocenyl-substituted ethenes and dibenzofulvenes

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Journal Information

Published in Journal of Sulfur Chemistry, 2018

Grzegorz Mlostoń, Róża Hamera-Fałdyga, Heinz Heimgartner

As demonstrated in a series of publications from the last three decades, thioketones 1 react as superior dipolarophiles in [3 + 2]-cycloadditions with diazomethane (CH2N2, 2a) and its derivatives [1–3]. Cycloaliphatic and aliphatic thioketones such as 2,2,4,4-tetramethyl-3-thioxocyclobutanone (1a), adamantanethione (1b) and di(tert-butyl)thioketone (1c) react with 2a regioselectively yielding 2,5-dihydro-1,3,4-thiadiazoles 3 as exclusive or major products and relatively stable compounds (Scheme 1).