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Noland WE, Konkel MJ, Konkel LM, et al. Structure Determination of the Products from the Acid-Catalyzed Condensation of Indole with Acetone. J Org Chem. 1996;61(2):451-454doi: 10.1021/jo951596p.
Noland, W. E., Konkel, M. J., Konkel, L. M., Pearce, B. C., Barnes, C. L., & Schlemper, E. O. (1996). Structure Determination of the Products from the Acid-Catalyzed Condensation of Indole with Acetone. The Journal of organic chemistry, 61(2), 451-454. https://doi.org/10.1021/jo951596p
Noland, Wayland E., et al. "Structure Determination of the Products from the Acid-Catalyzed Condensation of Indole with Acetone." The Journal of organic chemistry vol. 61,2 (1996): 451-454. doi: https://doi.org/10.1021/jo951596p
Noland WE, Konkel MJ, Konkel LM, Pearce BC, Barnes CL, Schlemper EO. Structure Determination of the Products from the Acid-Catalyzed Condensation of Indole with Acetone. J Org Chem. 1996 Jan 26;61(2):451-454. doi: 10.1021/jo951596p. PMID: 11666959.
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J Org Chem. 1996 Jan 26;61(2):451-454. doi: 10.1021/jo951596p.

Structure Determination of the Products from the Acid-Catalyzed Condensation of Indole with Acetone.

The Journal of organic chemistry

Wayland E. Noland, Michael J. Konkel, Lisa M. C. Konkel, Bradley C. Pearce, Charles L. Barnes, Elmer O. Schlemper

Affiliations

  1. College of Arts and Sciences, Department of Chemistry, University of Missouri-Columbia, 123 Chemistry Building, Columbia, Missouri 65211.

PMID: 11666959 DOI: 10.1021/jo951596p

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).

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