Synlett 2004(1): 192-194  
DOI: 10.1055/s-2003-43348
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© Georg Thieme Verlag Stuttgart · New York

Revisiting Cyclobutadienemetal Complexes: High-Content Dewar Benzene Polymers and a One-Pot Synthesis of Permethylated Ladderanes

Michael J. Marsella*, Samia Estassi, Li-Sheng Wang, Kunsang Yoon
Department of Chemistry, University of California at Riverside, Riverside, California, 92521-0403 USA
Fax: +1(909)7872435; e-Mail: Michael.marsella@ucr.edu;
Further Information

Publication History

Received 11 September 2003
Publication Date:
26 November 2003 (online)

Abstract

High-content Dewar benzene polymers and sterically congested [n]-ladderanes have been synthesized from [4πs+2πs] cyclobutadienemetal complex cycloaddition chemistry. In the former case, tetramethylcyclobutadiene-AlCl3 is reacted with an acetyl­ene-containing precursor polymer to yield > 95% Dewar benzene incorporation. In the latter case, [n]-ladderanes containing up to thirteen rings are prepared via a one-pot procedure from 2-butyne.

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Calculations were performed using Titan computational software, Schrodinger, Inc., 1500 SW First Avenue, Suite 1180, Portland, Oregon 97201.