G. Bassioni, F. Delgado, Matthieu Jaeggy
Nov 1, 2005
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Journal
Zeitschrift für Naturforschung B
Abstract
9-Oxabicyclo[3.3.1]nona-2, 6-diene (3) has been synthesized from cycloocta-1, 5-diene in two steps in an overall yield of 88%. The dihedral-angle dependence of its 1H solution NMR data and the double signal set of its 13C CP MAS NMR spectrum correspond to the results of the single crystal structure analysis. Reaction of 3 with N-bromosuccinimide in the presence of sodium peroxodisulfate or benzoylperoxide has led in good yield to a dibromo derivative 4, and a tribromo derivative 5, respectively. Compounds 4 and 5 feature two allylic bromine substituents, while an additional vinylic bromine atom is present in 5. According to a single crystal structure study the lattice of 4 consists of pairs of enantiomers similar to those found in the case of 3.