Intramolecular alkene Friedel-Crafts cyclization of 1-allyl-1-N-(ortho- alkylphenylamino)cyclohexanes. A useful route to alkyl substituted dihydrospiro[(1H)quinoline-2,1′-cyclohexanes]. Unprecedented ipso-substitution of alkyl groups

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 1981-1984

  Kouznetsov, Vladimir V ^a   Zubkov, Fedor I ^b   Nikitina, Eugenia V ^b   Duarte, Luz Dary Avellaneda ^a  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

^b PEOPLES FRIENDSHIP UNIVERSITY OF RUSSIA   (Russian Federation)

Author keywords

Intramolecular Friedel Crafts reaction; ipso Intramolecular electrophilic alkylation; Spiroquinolines

Indexed keywords

CYCLOHEXANE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; FRIEDEL CRAFTS REACTION; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 1242271358     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.148     Document Type: Article

References (21)

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16. All starting and final compounds ( 1a-d , 2a-d , 3b , 5 ) were fully characterized by spectral and elemental analyses. Crystallographic data for structures 3b and 5 have been deposited with the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication numbers CCDC 220116 ( 3b ) and 220117 ( 5 ). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44-1223-336-033; e-mail: deposit@ccdc.cam.ac.uk ).
17. Both crystallographic independent cations A and B have similar geometrical parameters but different orientations of the ethyl group [torsion angles C(9)C(10)C(16)C(17) and C(11)C(10)C(16)C(17)], 154.6°and -30.3°, in A ; and -123.4°and 53.8°in B , respectively.
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21. int=0.1238) reflections, GOOF=1.096.