Esters, acyloximes, amides and acid anhydrides have been prepared from the respective carboxylic acids, oximes, amines and alcohols by the use of the reagent combination BrCCl 3 -PPh 3 . The reactions obviate the handling acyl halides or more aggressive reagents PCl 3 , POCl 3 , or SOCl 2 . Furthermore, the environmentally hazardous CCl 4 used in Appel-type reactions is replaced with BrCCl 3 , a reagent of less environmental concern.
Benzamides were converted into benzonitriles with BrCCl 3 -PPh 3 -Et 3 N in CH 2 Cl 2 in an Appel-type reaction. Benzaldoximes could be transformed to benzonitriles under identical conditions. It was found that the reaction system BrCCl 3 -(2 equiv.)PPh 3 was also suitable for these transformations with PPh 3 replacing Et 3 N.
In the title molecule, C10H13NO2, the amide –NH2 group is oriented toward the propoxy substituent and an intramolecular N—H⋯O hydrogen bond is formed between the N—H group and the propoxy O atom. The benzene ring forms dihedral angles of 12.41 (2) and 3.26 (2)° with the amide and propoxy group mean planes, respectively. In the crystal, N—H⋯O hydrogen bonds order pairs of molecules with their molecular planes parallel, but at an offset of 0.73 (2) Å to each other. These pairs are ordered into two types of symmetry-related columns extended along the a axis with the mean plane of a pair in one column approximately parallel to (-122) and in the other to (-1-22). The two planes form dihedral angle of 84.40 (1)°. Overall, in a three-dimensional network, the hydrogen-bonded pairs of molecules are either located in (-1-22) or (-122) layers. In one layer, each pair is involved in four C—H⋯O contacts, twice as a donor and twice as an acceptor. Additionally, there is a short C—H⋯C contact between a benzene C—H group and the amide π-system.
In the asymmetric unit of the title compound, C19H16O2, there are two symmetry-independent molecules (A and B) that differ in the conformation of the ester ethoxy group. In the crystal, the molecules form inversion dimers via pairs of C—H⋯O interactions. Within the dimers, the anthracenyl units have interplanar distances of 0.528 (2) and 0.479 (2) Å for dimers of molecules A and B, respectively. Another short C—H⋯O contact between symmetry-independent dimers links them into columns parallel to [10-1]. These columns are arranged into (111) layers and there are π–π stacking interactions [centroid–centroid distances = 3.6446 (15) and 3.6531 (15) Å] between the anthracenyl units from the neighbouring columns. In addition, there are C—H⋯π interactions between the anthracenyl unit of dimers A and dimers B within the same column.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.