title: Structure Determination of the Products from the Acid-Catalyzed Condensation of Indole with Acetone.
abstract: Four of the previously reported compounds obtained from the acid-catalyzed condensation of indole with acetone are now assigned the following structures: cis-4,4a,9,9a-tetrahydro-2-(1H-indol-3-yl)-4,4-dimethyl-3H-carbazole (2a), 1,1',4,4'-tetrahydro-1,1,1',1'-tetramethyl-3,3'(2H,2'H)-spirobi[cyclopent[b]indole] (4), 4,4a-dihydro-2-(3-1H-indolyl)-4,4-dimethyl-3H-carbazol-4a-ol (7), and 5-(2-aminophenyl)-1,3,4,5-tetrahydro-1,1,4,4-tetramethylcyclopent[kl]acridine (8). The structure of the novel rearrangement product 8 was solved by an X-ray crystal structure determination. The two previously reported autoxidation products of 4 are now assigned the following structures: 1,3',4,4'-tetrahydro-1,1,4',4'-tetramethyl-cis-dispiro[cyclopent[b]indole-3(2H),2'(5'H)-furan-5',3"-[3H]-indol]-2"(1"H)-one (5) and 1,4-dihydro-1,1,5',5'-tetramethylspiro[cyclopent[b]indole-3(2H),3'(4'H)-1-benzazocine]-2'(1'H),6'(5'H)-dione (6).
authors.affiliation: College of Arts and Sciences, Department of Chemistry, University of Missouri-Columbia, 123 Chemistry Building, Columbia, Missouri 65211.
authors.forename: Wayland E.
authors.initials: WE
authors.lastname: Noland
authors.forename: Michael J.
authors.initials: MJ
authors.lastname: Konkel
authors.forename: Lisa M. C.
authors.initials: LM
authors.lastname: Konkel
authors.forename: Bradley C.
authors.initials: BC
authors.lastname: Pearce
authors.forename: Charles L.
authors.initials: CL
authors.lastname: Barnes
authors.forename: Elmer O.
authors.initials: EO
authors.lastname: Schlemper