3530-62-9Relevant articles and documents
A solid-state, solution, and theoretical structural study of kinetic and thermodynamic lithiated derivatives of a simple diazomethane and their reactivities towards aryl isothiocyanates
Armstrong, David R.,Davies, Robert P.,Haigh, Robert,Hendy, Mark A.,Raithby, Paul R.,Snaith, Ronald,Wheatley, Andrew E. H.
, p. 3363 - 3375 (2003)
(Trimethylsilyl)diazomethane (1-H) reacts with nBuLi in THF at elevated temperature to afford (previously reported) 1-Li·3/2 THF. However, reaction in hexane/TMEDA at low temperature affords instead the N-lithiate Me3SiCNNLi·TMEDA (9), which is a novel open pseudo-cubic tetramer in the solid state. Variable-temperature NMR spectroscopy suggests that N-metallated 9, apparently the kinetic product of the reaction, irreversibly rearranges at high temperature in solution to give the thermodynamically preferred C-lithiated isomer. These observations, supported by DFT calculations, influence our understanding of the reactivity of lithiated diazomethanes towards aryl isothiocyanates, suggesting as they do that previously observed product selectivity in these reactions is critically dependent on temperature control exercised during the process. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
Preparation of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles via chemoselective сyclocondensation of electrophilically activated nitroalkanes to (thio)semicarbazides or thiohydrazides
Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Arutiunov, Nikolai A.,Kirillov, Nikita K.,Rubin, Michael
, p. 1067 - 1072 (2020/10/02)
[Figure not available: see fulltext.] Unusual reaction proceeding via the electrophilic activation of nitroalkanes in the presence of polyphosphoric acid has been discovered. Subsequent nucleophilic attack with semicarbazides or thiosemicarbazides allows
New Cyclizing Reagent for the Synthesis of 1,3,4-Thiadiazoles
Yarovenko, Vladimir N.,Shirokov, Aleksandr V.,Zavarzin, Igor V.,Krupinova, Oksana N.,Ignatenko, Anatolii V.,Krayushkin, Mikhail M.
, p. 17 - 19 (2007/10/03)
A new cyclizing reagent is proposed for the synthesis of 5-unsubstituted 1,3,4-thiadiazoles. The latter are formed in good yields by the reactions of thiohydrazides with diethyl chlorophosphate in DMF.