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

作者: Kim C. Pich , Roger Bishop , Donald C. Craig , Marcia L. Scudder

DOI: 10.1007/BF00705818

关键词: AmideAcetamideStereochemistryHydrogen bondAcetonitrileMoleculeRitter reactionMedicinal chemistryCrystal structureInclusion compoundChemistry

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

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