Ritter reactions. VIII. Inclusion compounds formed betweenN-(5H-Dibenzo[a, d]cycloheptyl)acetamides and dioxane

Research paper by Kim C. Pich, Roger Bishop, Donald C. Craig, Marcia L. Scudder

Indexed on: 01 Jun '94Published on: 01 Jun '94Published in: Journal of Inclusion Phenomena and Macrocyclic Chemistry


5H-Dibenzo[a, d]cyclohepten-5-ol2 and its saturated analogue4 undergo Ritter reactions with acetonitrile and sulfuric acid to afford the acetamide derivatives3 or5 respectively. Both products form unstable inclusion compounds when crystallised from dioxane. The crystal structure of the dioxane compound of3 is reported. This material [(C17H15NO)·(C4H8O2)2,Pnma,a=9.616(1),b=23.280(2),c=10.298(1) Å,Z=4,R=0.054] has the amide molecules arranged in parallel chains by means of intermolecular −N−H⋯O=C hydrogen bonds. The inclusion compound is stabilised by means of −C−H⋯O-hydrogen bonds. Each dioxane molecule is involved in five such interactions to neighbouring molecules of3 and dioxane.