Synthetic studies of cis-3a-aryloctahydroindole derivatives by copper- catalyzed cyclization of N-allyltrichloroacetamides: Facile construction of benzylic quaternary carbons by carbon-carbon bond-forming reactions

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9625-9631

  Iwamatsu, Sho Ichi ^a   Matsubara, Kouki ^a   Nagashima, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE; COPPER; INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY SPECTROMETRY;

EID: 0033601284     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9912146     Document Type: Article

References (61)

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59. We carried out crystallographic analysis of 24a and 24b. The molecular structure of 24a showed that very effective resonance stabilization provided that six atoms, C2, C1, O1, N1, C3, and C6, lie on the same plane in the molecular structure of 24a. The C-O distance is substantially longer than the usual C=O distances, whereas the N-CO bond length is shorter than normal N-C single bond distances (N-CO; 1.35 Å (1), C+O.; 1.24 Å (1)). Thus, the N-CO bond of 24a has a considerable double-bond character like A. Since X-ray analysis of 24b did not converge well (R = 7.7%), precise comparison of the structure of 24b with that of 24a is difficult. However, it is noteworthy that the molecular structure suggested a single bond character of N-CO bond (N-CO; 1.375 Å (4), C=O.; 1.195 Å (1)). Five atoms, C1, N1, C3, S1, and 03, lie on the same plane, which makes an angle of 13° with a plane consisting of C2, C1, and O1. We consider that the resonance structure shown as B is responsible for facile rotation of the CO-N bond in 24b. (Matrix Presented)
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