Syntheses of cyclopentadienyl annulated imidazol-2-ylidenes

ORGN 360

Anthony J. Arduengo III and Oana A. Cojocaru, oacojocaru@bama.ua.edu. Department of Chemistry, University of Alabama, 250 Hackberry Lane, Shelby Hall, Tuscaloosa, AL 35401
In 2005 Arduengo and co-workers reported the synthesis of “the first directly annulated cyclopentadienyl imidazolium salt” (1).1 Metallic complexes containing the cyclopentadienyl annulated imidazol-2-ylidene moiety were synthesized and characterized.2,3,4 The bicyclic 4,6-bis(4-chlorophenyl)-1,3-dimethylcyclopentadienyl[d]imidazole -2-thione (2) is a convenient precursor to imidazolocyclopentadienes. The absence of a substituent at position 6 provides important flexibility for studying substituent effects and affords the opportunity to incorporate the bicycle into polymeric structures. The synthesis and chemistry of 2 will be described.



* We gratefully acknowledge support for this research from the National Science Foundation (CHE-0413521 and CHE 0115760) and E. I. du Pont de Nemours and Co., Inc.

1) Arduengo, A. J.; Bannenberg, T. P.; Ţapu, D.; Marshall, W. J. Tetrahedron Lett. 2005, 46, 6847-6850.

2) Arduengo, A. J., III; Ţapu, D.; Marshall, W. J. J. Am. Chem. Soc. 2005, 127, 16400-16401.

3) Arduengo, A. J., III; Ţapu, D.; Marshall, W. J. Angew. Chem., Int. Ed. 2005, 44, 7240-7244.

4) Arduengo, A. J., III; Bannenberg, T. P.; Ţapu, D.; Marshall, W. J. Chem. Lett. 2005, 34, 1010-1011.



 

Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008