Unexpected chlorination of angularly annelated [2.2]paracyclophanes during DDQ oxidation

Tetrahedron Letters

Volumn 46, Issue 6, 2005, Pages 949-950

  Minuti, Lucio ^a   Taticchi, Aldo ^a   Marrocchi, Assunta ^a   Lanari, Daniela ^a   Gacs Baitz, Eszter ^b   Gomory, Agnes ^b  

^a UNIVERSITY OF PERUGIA   (Italy)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

Author keywords

2.2 Paracyclophanes; Chlorination; Oxidation

Indexed keywords

CHLORINE; CYCLOPHANE DERIVATIVE; OXIDIZING AGENT;

ARTICLE; CHLORINATION; DIELS ALDER REACTION; IONIZATION; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; OXIDATION;

BETULACEAE;

EID: 12344325444     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.049     Document Type: Article

References (13)

1. Inter alia: L. Minuti, A. Taticchi, A. Marrocchi, L. Costantini, and E. Gacs-Baitz Tetrahedron: Asymmetry 12 2001 1179 1183
2. A. Marrocchi, L. Minuti, A. Taticchi, I. Dix, H. Hopf, E. Gacs-Baitz, and P.G. Jones Eur. J. Org. Chem. 2001 4259 4268
3. D. Lanari, A. Marrocchi, L. Minuti, A. Taticchi, and E. Gacs-Baitz Tetrahedron: Asymmetry 13 2002 1331 1335
4. L. Minuti, A. Taticchi, A. Marrocchi, D. Lanari, A. Broggi, and E. Gacs-Baitz Tetrahedron: Asymmetry 14 2003 481 487
5. 2: C, 75.45; H, 4.87. Found: C, 75.40; H, 4.89
6. R.L. Shriner, R.C. Fuson, D.Y. Curtin, and T.C. Morril The Systematic Identification of Organic Compounds 1980 John Wiley and Sons New York pp 81-82
7. 2: C, 75.45; H, 4.87. Found: C, 75.40; H, 4.89
8. Inter alia: E. Gacs-Baitz, L. Minuti, and A. Taticchi Tetrahedron 50 1994 10359 10366
9. L. Minuti, A. Taticchi, A. Marrocchi, G. Morozzi, L. Pampanella, and E. Gacs-Baitz Polycyclic Aromat. Compd. 13 1999 9 24
10. L. Minuti, A. Taticchi, A. Marrocchi, and E. Gacs-Baitz Synth. Commun. 28 1998 2181 2190
11. A. Taticchi, L. Minuti, D. Lanari, A. Marrocchi, I. Tesei, and E. Gacs-Baitz Tetrahedron 60 2004 11759 11764
12. DDQ treatment of compounds 3. A toluene solution (25 mL) of the aromatic compounds 3a or 3b [6] (0.052 mmol) and DDQ (0.09 mmol) was heated at reflux temperature and the course of the reaction was checked by analysing a small aliquot of the reaction mixture at different times. After 24 h the reaction mixture was worked up as usual. All the TLC analyses showed that only the reactants were present in the reaction mixture
13. P.V.P. Pragnacharyulu, and E. Abushanab Tetrahedron Lett. 38 1997 3683 3686