286 The [5+5]-Route for Hydronaphthalene Ring Synthesis Using Fischer Carbenes and Highly Conjugated Alkynes

Thursday, November 5, 2009: 2:20 PM
Longhorn (Camino Real Hotel)
James W. Herndon , Department of Chemistry & Biochemistry, New Mexico State University, Las Cruces, NM
Rajesh Kumar-Patti , Department of Chemistry & Biochemistry, New Mexico State University, Las Cruces, NM
Lalith Ranchigoda-Gamage , Department of Chemistry & Biochemistry, New Mexico State University, Las Cruces, NM
Shaofeng Duan , Department of Chemistry & Biochemistry, New Mexico State University, Las Cruces, NM
Kris Waynant , Department of Chemistry & Biochemistry, New Mexico State University, Las Cruces, NM
Dilip Sinha-Mahapatra , Department of Chemistry & Biochemistry, New Mexico State University, Las Cruces, NM
Zhipeng Wang , Department of Chemistry & Biochemistry, New Mexico State University, Las Cruces, NM
Rongti Li , Department of Chemistry & Biochemistry, New Mexico State University, Las Cruces, NM
Alejandro Camacho-Davila , Department of Chemistry & Biochemistry, New Mexico State University, Las Cruces, NM
Alfreda Nelson , Department of Chemistry & Biochemistry, New Mexico State University, Las Cruces, NM

The coupling of Fischer carbene complexes that feature unsaturation in the γ,d-position with enyne-carbonyl systems initiates a series of complex tandem events that ultimately culminates in a new hydronaphthalene ring system.  This approach to the synthesis of naphthalenes is highly novel and unusual in that each of the five-carbon pieces contributes carbons to both rings of new ring system.  The scope and limit of this process as well as examples relevant to organic synthesis will be discussed.

El Paso ACS 2009.gif