104942-78-1Relevant articles and documents
The Synthesis of Hetero-bridged (3,6)Oxepinophanes
Jenneskens, Leonardus W.,Kostermans, Gerardus B. M.,Brink, Harmannus J. ten,Wolf, Willem H. de,Bickelhaupt, Friedrich
, p. 2119 - 2122 (2007/10/02)
The (3,6)oxepinophanes (8) are the oxepines with the shortest bridge reported so far.They were obtained starting from diethyl furan-3,4-dicarboxylate (3) which, with lithium aluminium hydride, afforded the diol (4); this was converted into the seven-membered siloxanes (5a and b) by reaction with dichlorodimethylsilane or dichlorodimesitylsilane, respectively.By the Prinzbach-Tochtermann sequence, compounds (5) were converted into the oxepinophanes (8) in three steps: Diels-Alder reaction of (5) with dimethyl acetylenedicarboxylate to give the fused 7-oxanobornadienes (6), photochemical transformations of compounds (6) to the fused 7-oxaquadricyclanes (7), and thermal isomerization of compounds (7) to (8).Attempted conversion of (8a) into (11a), a derivative of paracyclophane, was unsuccessful.