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Note | Regular issue | Vol 57, No. 8, 2002, pp.1513-1524
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9534
Synthesis of 2,2’,2”,2”’-(1,2- Ethanediylidene)tetrafuran and Diels-Alder Reaction with Dimethyl Acetylenedicarboxylate

Marc-Etienne Schwenter, Kurt Schenk, Rosario Scopelliti, and Pierre Vogel*

*Institute of Molecular and Biological Chemistry, Swiss Federal Institute of Technology, EPFL-BCH, CH-1015 Lausanne-Dorigny, Switzerland

Abstract

A one step procedure has been found that converts 2,2’-methylenedifuran (1) into 2,2,’,2”,2”’-(1,2-ethanediylidene)tetrafuran (4: 1,1,2,2-tetrakis(furan-2-yl)ethane). This compound adopts two similar C2V-symmetrical conformations (4A and 4A’) in the crystalline state in which the C-H bond of the 1,2-ethanediylidene moieties is anti-periplanar with the C(2)-O bond of the vicinal furan-2-yl groups. Tetrafuran (4) is little reactive toward dienophiles with normal electronic demand. With dimethyl acetylenedicarboxylate a single 1:1 adduct (8) (dimethyl (1RS,2RS,2aRS,5SR,5aRS,6RS,8aRS,8bSR)-1,2-di(furan-2-yl)-1,2-dihydro-5H,6H-2a,5:6,8a-diepoxyacenaphthylene-5a,8b-dicarboxylate) was isolated. Its structure was established by single crystal X-Ray radiocrystallography.