Synthesis and Intramolecular Diels-Alder Reaction of 4-Trimethylsiloxy-1, 3, 8-nonatriene
Oxy-Cope rearrangement of 4-vinyl-1, .6-heptadien-4-ol  at 330°C gave 1, 8-nonadien-4one  along with 2, 8-nonadien-4-one . The ketone  was converted to the title compound  as a mixture of (E)- and (Z)-isomers, by the treatment with LDA and, trimethylsilyl chloride. Alternatively the nonatriene  was prepared selectively by the anionic oxy-Cope rearrangement of  followed by quenching with trimethylsilyl chloride. Intramolecular Diels-Alder reaction of  afforded only cis-3 a-trimethylsiloxy-2, 3, 3 a, 6, 7, 7 a-hexahydro-1 H-indene , irrespective of the stereochemistry of .
Journal of the Chemical Society of Japan : chemistry and industrial chemistry
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Copyright (c) 1987 The Chemical Society of Japan
Graduate School of Engineering