5578-84-7Relevant academic research and scientific papers
Introducing catalytic lossen rearrangements: Sustainable access to carbamates and amines
Kreye, Oliver,Wald, Sarah,Meier, Michael A. R.
supporting information, p. 81 - 86 (2013/03/13)
A new, highly efficient and environmentally benign catalytic variant of the Lossen rearrangement is described. Dimethyl carbonate (DMC) as green activation reagent of hydroxamic acids in presence of catalytic amounts of tertiary amine bases {1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), 1,8-biazabicyclo 5.4.0 undec-7-ene (DBU), 1,4-diazabicyclo[2.2.2]octane (DABCO), and triethylamine} and small quantities of methanol initiate the rearrangement. Methyl carbamates were obtained in good to moderate yields when aliphatic hydroxamic acids were employed in this catalytic Lossen rearrangement; under the same conditions aromatic hydroxamic acids yielded anilines. Notably, the mixture of DMC/methanol was recycled several times without observing decreased yields, thus minimizing the produced waste. Moreover, several other organic carbonates were successfully employed in the introduced catalytic Lossen rearrangement procedure. Copyright
Conformational behaviour of hydroxamic acids: Ab initio and structural studies
Brown, David A.,Coogan, Raymond A.,Fitzpatrick, Noel J.,Glass, William K.,Abukshima, Dau E.,Shiels, Loreto,Ahlgren, Markku,Smolander, Kimmo,Pakkanen, Tuula T.,Pakkanen, Tapani A.,Peraekylae, Mikael
, p. 2673 - 2679 (2007/10/03)
The conformational behaviour of a series of monohydroxamic acids, p-RC6H4CONR 'OH (R = Me, R' = H Me; R = MeO, R' = H, Me; R = NO2, R' = H), and a series of dihydroxamic acids, (CH2)n (CONR'OH)2 (n = 3-8, 10, R' = H and n = 7, R' = Me), in methanol, DMSO and chloroform and in the solid state has been examined using IR and NMR spectroscopy. X-Ray crystal structure determinations of p-MeC6H4CONMeOH and the monohydrate of glutarodihydroxamic acid (n = 3) together with ab initio molecular orbital calculations for several hydrated and unhydrated hydroxamic acids have been performed. Hydrogen bonding effects are shown to be important in both the so id state and solution. The cis(Z) conformation of the hydroxamate group(s) (CONHOH) is preferentially stabilized by hydrogen bonding with water molecules.
A FACILE SYNTHESIS OF ALIPHATIC DIHYDROXAMIC ACIDS OF GENERAL FORMULA RONR'-CO-(CH2)n-CO-NR'OR
Brown, D. A.,Geraty, R. A.,Glennon, J. D.,Choileain, N. Ni
, p. 1159 - 1164 (2007/10/02)
Synthesis of dihydroxamic acids using dicarboxylic acids and N,N'-carbonyldiimidazole.
