Synthesis of oxa-bridged derivatives from Diels-Alder bis-adducts of butadiene and 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene

Beilstein Journal of Organic Chemistry

Volumn 6, Issue , 2010, Pages

  Khan, Faiz Ahmed ^a   Parasuraman, Karuppasamy ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

3 sulfolene; Diels Alder reactions; Diketones; Oxa bridged derivatives; Ruthenium

Indexed keywords

EID: 77956836821     PISSN: 18605397     EISSN: 18605397     Source Type: Journal    
DOI: 10.3762/bjoc.6.64     Document Type: Article

References (23)

1. Fieser, L. F.; Fieser, M. Reagent for organic synthesis; Wiley: New York, 1969; Vol.2, p 390.
2. Sample, T. E., Jr..; Hatch, L. F. Org. Synth. 1988, 6, 454.
3. Chou, T.-S.; Tso, H.-H. Org. Prep. Proced. Int. 1989, 21, 259-296.
4. Forman, M. A.; Dailey, W. P. J. Org. Chem. 1993, 58, 1501-1507. doi:10.1021/jo00058a035
5. Garcia, J. G.; Fronczek, F. R.; McLaughlin, M. L. Tetrahedron Lett. 1991, 32, 3289-3292. doi:10.1016/S0040-4039(00)92688-1
6. Garcia, J. G.; McLaughlin, M. L. Tetrahedron Lett. 1991, 32, 3293-3296. doi:10.1016/S0040-4039(00)92689-3
7. Khan, F. A.; Dash, J.; Sudheer, Ch.; Sahu, N.; Parasuraman, K. J. Org. Chem. 2005, 70, 7565-7577. doi:10.1021/jo0507385 (Pubitemid 41318516)
8. Khan, F. A.; Dash, J. J. Am. Chem. Soc. 2002, 124, 2424-2425. doi:10.1021/ja017371f (Pubitemid 34251742)
9. Khan, F. A.; Dash, J.; Sahu, N.; Sudheer, Ch. J. Org. Chem. 2002, 67, 3783-3787. doi:10.1021/jo025521e (Pubitemid 34563991)
10. Khan, F. A.; Dash, J. J. Org. Chem. 2003, 68, 4556-4559. doi:10.1021/jo034023i (Pubitemid 36622754)
11. Khan, F. A.; Satapathy, R.; Dash, J.; Savitha, G. J. Org. Chem. 2004, 69, 5295-5301. doi:10.1021/jo049615v (Pubitemid 39014360)
12. Khan, F. A.; Rout, B. Tetrahedron Lett. 2006, 47, 5251-5253. doi:10.1016/j.tetlet.2006.05.156
13. Khan, F. A.; Rout, B. J. Org. Chem. 2007, 72, 7011-7013. doi:10.1021/jo0710127 (Pubitemid 47434922)
14. Khan, F. A.; Parasuraman, K.; Sadhu, K. K. Chem. Commun. 2009, 2399-2401. doi:10.1039/b820479a
15. Peri, C. A. Gazz. Chim. Ital. 1955, 85, 1118.
16. Chem. Abstr. 1956, 50, 10013.
17. Nigmatova, V. B.; Zaitsev, Y. V.; Anfilogova, S. N.; Pekhk, T. I.; Belikova, N. A. Russ. J. Org. Chem. 1994, 30, 727-732.
18. JAI LC-908W preparative HPLC equipped with a JAIGEL-OA4100 column (Japan Analytical Industry Co. Ltd.).
19. Khan, F. A.; Prabhudas, B.; Dash, J.; Sahu, N. J. Am. Chem. Soc. 2000, 122, 9558-9559. doi:10.1021/ja001956c
20. Khan, F. A.; Sahu, N. J. Catal. 2005, 231, 438-442. doi:10.1016/j.jcat. 2005.02.001
21. -3, respectively. CCDC: 763534 contain the supplementary crystallographic data for the compounds 8. This data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or mail to: deposit@ccdc.cam.ac.uk.
22. Veliev, M. G.; Chalabieva, A. Z.; Shatirova, M. I.; Mamedov, E. Sh.; Mamedov, I. M. Russ. J. Org. Chem. 2001, 37, 223-229. doi:10.1023/A: 1012326912373
23. Veliev, M. G.; Chalabieva, A. Z.; Mamedova, A. F. Russ. J. Org. Chem. 2009, 45, 650-659.