2840-20-2Relevant academic research and scientific papers
Synthesis of alkylammonium tosylates with poly{[4-hydroxy(tosyloxy)iodo] styrene}
Liu, Shi Juan,Zhang, Ji Zhen,Tian, Guan Rong,Liu, Ping
, p. 823 - 827 (2007/10/03)
Several primary carboxamides (RCONH2) were converted to the corresponding alkylammonium tosylates (RN+H3 -OTs) with poly{[4-hydroxy (tosyloxy) iodo]styrene} (PSHTIB) in yields ranging from 60% to 90%.
New upper rim pyridine-bridged calix[4]arenes: Synthesis and complexation properties toward neutral molecules and ammonium ions in organic media
Arduini, Arturo,McGregor, William M.,Pochini, Andrea,Secchi, Andrea,Ugozzoli, Franco,Ungaro, Rocco
, p. 6881 - 6887 (2007/10/03)
A new series of calix[4]arenes, diametrically bridged at the upper rim with pyridino systems, has been synthesized. The shape, rigidity, and chemical structure of the bridge influence the host-guest complexation properties of these systems in solution toward several neutral molecules having acidic C-H bonds. Additionally, selective complexation of methylammonium tosylate in comparison with other ammonium salts has been observed and the strength of this complexation enhanced by electron-donor ability of the p-substituent on the pyridine moiety of the calixarene host. X-ray crystal structures of endo complexes of host 5 with malononitrile and nitromethane have been resolved, verifying specific C-H bonding with the hard oxygen and nitrogen atoms of the bridge and the soft aromatic ring of the calixarene.
Direct Conversion of Aliphatic Carboxamides to Alkylammonium Tosylates with benzene
Lazbin, I. Mark,Koser, Gerald F.
, p. 2669 - 2671 (2007/10/02)
The utility of benzene (2) as a "Hofmann reagent" has been explored.Treatment of various primary, aliphatic carboxamides (RCONH2, R = methyl, ethyl, isopropyl, tert-butyl, n-pentyl, n-heptyl, undecyl, allyl, benzyl, cyclobutyl, cyclohexyl) with 2 in acetonitrile at reflux gave the corresponding alkylammonium tosylates (RN+H3-OTs) in yields ranging from 57percent to 94percent.The alkylammonium tosylates separated directly from the solvent when the reaction mixtures were kept at room temperature or below.When α-phenylacetamide was allowed to react with 2 in ethanol, ethyl benzylcarbamate (4) was obtained in 50percent yield, a result consistent with the intermediate existence of benzyl isocyanate in this reaction.A mechanism for the conversion of carboxamides by 2 to alkylammonium tosylates, involving the initial formation of N-phenyl iodonio amides and their collapse to iodobenzene and alkyl isocyanates, is proposed.The reaction of malonamide with 2 in acetonitrile followed a divergent course: 2-(tosyloxy)malonamide (3) was obtained in ca. 81percent yield (crude).
