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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 9
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Original Articles

Synthesis of Substituted Tricyclo[5.3.1.04,9]undecan‐2,6‐dione from 4,4‐Disubstituted Cyclohexanone Enamines and Methacryloyl Chloride

Syeda Asghari Ahmed Department of Chemistry, University of Dhaka, Dhaka, Bangladesh
,
Kawsari Akhter Department of Chemistry, University of Dhaka, Dhaka, Bangladesh
,
Yoshisuke Tsuda Faculty of Pharmaceutical Sciences, Kanazawa University, Kanazawa, Japan
,
M. Mahmun Hossain Department of Chemistry, University of Wisconsin—Milwaukee, Milwaukee, Wisconsin, USA
,
F. Holger Forsterling Department of Chemistry, University of Wisconsin—Milwaukee, Milwaukee, Wisconsin, USA
&
M. Giasuddin Ahmed Department of Chemistry, University of Dhaka, Dhaka, BangladeshCorrespondence[email protected]
Pages 1273-1283 | Received 09 Sep 2005, Published online: 24 Feb 2007

References

  • Ahmed , M. G. , Moeiz , S. M. I. , Ahmed , S. A. , Kiuchi , F. and Tsuda , Y. 2001 . Synthesis of substituted tricyclo[5.3.1.04,9]undecane‐2,6‐dione . Tetrarhedron , : 3143 – 3150 .
  • Ahmed , M. G. , Moeiz , S. M. I. , Ahmed , S. A. , Kiuchi , F. , Tsuda , Y. and Sampson , P. J. 1999 . Synthesis of some substituted 2,4‐adamantanedione from 4,4‐disubstituted cyclohexanone enamines and α,β‐unsaturated acid chlorides . J. Chem. Res. , : 316 – 317 . Syn., Miniprint, 1439–1470
  • Huque , A. K. M. F. , Mosihuzzaman , M. , Ahmed , S. A. , Ahmed , M. G. and Andersson , R. 1987 . Synthesis of some substituted adamantane‐2,4‐diones . J. Chem. Res. , : 214 – 215 . Synop., Miniprint, 1701–1710
  • Ahmed , M. G. , Huque , A. K. M. F. , Ahmed , S. A. , Mosihuzzaman , M. and Andersson , R. 1988 . Reaction of α,β‐unsaturated acid chlorides with 4,4‐disubstituted cyclohexanone enamines . J. Chem. Res. , : 362 – 363 . Synop., Miniprint, 2815–2835
  • Bruson , H. A. and Riener , T. W. 1942 . Chemistry of acrylonitrile: II, reaction with ketones . J. Am. Chem. Soc. , 64 : 2850 – 2858 .
  • Chapman , N. B. , Sotheeswaran , S. and Toyne , K. J. 1970 . Preparation of 4‐substituted 1‐methoxycarbonylbicyclo[2.2.2]octanes, 4‐substituted 1‐phenylbicyclo[2.2.2]octanes, 4‐substituted 1‐p‐nitrophenylbicyclo[2.2.2]octanes and 1,4‐disubstituted bicycle[2.2.2]octanes . J. Org. Chem. , 35 : 917 – 923 .
  • Ahmed , M. G. , Ahmed , S. A. , Akhter , K. , Moeiz , S. M. I. , Tsuda , Y. , Kiuchi , F. , Hossain , M. M. and Forsterling , F. H. 2005 . Synthesis of some substituted adamantane‐2,4‐diones from 4,4‐disubstituted cyclohexanone enamines and methacryloyl chloride . J. Chem. Res. , in press
  • Duddeck , H. and Klein , H. 1977 . 13C nuclear magnetic spectra—VI, stereochemical dependence of γanti′ heterosubstituent effects on 13C chemical shifts of bridgehead substituted molecules . Tetrahedron , 33 : 1971 – 1977 .
  • Bruson , H. A. and Riener , T. W. 1943 . Chemistry of acrylonitrile: III, cyanomethylation of α,β‐unsaturated compounds . J. Chem. Soc. , 65 : 18 – 23 .
  • Colonge , J. and Vuillemet , R. 1961 . The bicyclo[2.2.2]octane series . Bull. Soc. Chim. Fr. , : 2235 – 2238 .

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