Dearomatization reactions of aryl-substituted silaaziridines

Journal of Organic Chemistry

Volumn 73, Issue 20, 2008, Pages 8113-8115

  Nevárez, Zulimar ^a   Woerpel, K A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES;

ARYL GROUPS; CHEMICAL EQUATIONS; DEAROMATIZATION; DIASTEREO-SELECTIVITY; NITROGEN ATOMS; RING STRAINS;

CHEMICAL REACTIONS;

AZIRIDINE DERIVATIVE; BENZALDEHYDE; CARBON; NITROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILAAZIRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

AZIRIDINES; BENZALDEHYDES; CARBON; MOLECULAR STRUCTURE; NITROGEN; STEREOISOMERISM;

EID: 53849148281     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801502x     Document Type: Article

References (24)

1. Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196.
2. Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247-258.
3. Hoz has argued that orbital effects and ground state destabilization contribute to rate accelerations observed in reactions of strained rings: (a) Sella, A.; Basch, H.; Hoz, S. J. Am. Chem. Soc. 1996, 118, 416-420.
4. (b) Sella, A.; Basch, H.; Hoz, S. Tetrahedron Lett. 1996, 37, 5573-5576.
5. Cope rearrangements have been observed for aryl vinyl cyclopropanes: Barluenga, J.; Aznar, F.; Gutiérrez, I.; Martín, J. A. Org. Lett. 2002, 4, 2719-2722.
6. Weidenbruch, M.; Piel, H.; Peters, K.; von Schnering, H. G. Organometallics 1993, 12, 2881-2882.
7. Belzner, J.; Ihmels, H.; Pauletto, L.; Noltemeyer, M. J. Org. Chem. 1996, 61, 3315-3319.
8. Belzner, J.; Dehnert, U.; Ihmels, H. Tetrahedron 2001, 57, 511-517.
9. Nevárez, Z.; Woerpel, K. A. Org. Lett. 2007, 9, 3773-3776.
10. Seyferth, D.; Duncan, D. P.; Shannon, M. L. Organometallics 1984, 3, 579-583.
11. Bodnar, P. M.; Palmer, W. S.; Ridgway, B. H.; Shaw, J. T.; Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1997, 62, 4737-4745.
12. Franz, A. K.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 949-957.
13. Franz, A. K.; Woerpel, K. A. Angew. Chem., Int. Ed. 2000, 39, 4295-4299.
14. The sensitivity of this compound has thwarted our attempts to derivatize it by either reducing it or engaging the diene in cycloadditions. Under all conditions, either recovered starting materials or numerous decomposition products were observed.
15. The details of the crystallographic studies are provided as Supporting Information.
16. Sullivan, S. A.; DePuy, C. H.; Damrauer, R. J. Am. Chem. Soc. 1981, 103, 480-481.
17. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
18. Nielsen, I. M. B. J. Phys. Chem. A 1998, 102, 3193-3201.
19. Attempts to trap the ylide intermediate with either electron-rich alkenes (1-phenyl-1-trimethylsilyloxyethene) or electron-poor alkenes (acrylonitrile) were not successful; only aziridine 2 was observed.
20. Gordon, M. S.; Boatz, J. A.; Walsh, R. J. Phys. Chem. 1989, 93, 1584-1585.
21. Al-Rubaiey, N.; Carpenter, I. W.; Walsh, R.; Becerra, R.; Gordon, M. S. J. Phys. Chem. B 1998, 102, 8564-8572.
22. Lide, D. R. CRC Handbook of Chemistry and Physics, 84th ed.; CRC Press: New York, 2003-2004; pp 9-10-9-11.
23. Banks, H. D. J. Org. Chem. 2006, 71, 8089-8097.
24. Zora, M. J. Org. Chem. 2005, 70, 6018-6026.