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Paper | Special issue | Vol 88, No. 1, 2014, pp.521-534
Published online, 7th August, 2013
DOI: 10.3987/COM-13-S(S)76
A Thermal Potential [6+4] 2H-Transfer Reaction in a Cyclic Dimer of Dimethyl 2a,8a-Dihydrocyclopent[c,d]azulene-1,2-dicarboxylate

Peter Uebelhart, Erja Lehto, and Hans-Jürgen Hansen*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Abstract

Azulenes and dimethyl acetylenedicarboxylate (ADM) react under catalysis of diethylaluminum chloride (Et2AlCl) in toluene to corresponding 2a,8a-dihydrocyclopenta[cd]azulene-1,2-dicarboxylates, which on further influence of Et2AlCl dimerize by bond formation between the central C(8b) and C(8’b) atoms and inter alia C(3) and C(8’) atoms. The thus formed heptacyclic compounds undergo on heating in tetralin an intramolecular disproportionation by transfer of two H-atoms from one to the other part of the heptacyclic structures. The kinetics of this process is studied with partially deuterated heptacycles.