The synthesis of a homologous series of polyenes by the bis-Wittig-reaction of 1,8-bis(triphenylphosphoniomethyl)-naphthalene dibromide 3 with unsaturated aldehydes 2b and 2c leads, according to X-ray analyses, to the unexpected chiral hydrocarbons 4b and 4c owing to spontaneous intramolecular rearrangement; in contrast the shorter chain bis-diene 1a can be isolated by reaction of aldehyde 2a with phosphonium salt 3.
F. Vögtle, E. Schmohel and M. Nieger, J. Chem. Soc., Chem. Commun., 1993, 760 DOI: 10.1039/C39930000760
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