SCHEDULED MAINTENANCE
Palladium triggered diene formation from nitro allylic compounds: a versatile entry into naphthalene derivatives†
Sébastien
Prévost 
*a
and
Laurent
El Kaïm
*a
*a
and
Laurent
El Kaïm
*a
Abstract
Nitro allylic derivatives were converted into dienes through the elimination of the nitro group under basic treatment, in the presence of a palladium catalyst. This reaction probably involves the formation of a palladium π-allyl complex followed by a base-promoted β-hydride elimination. This reaction, combined with the condensation of ketones with nitromethane and the functionalization of the resulting nitrocycloalkenes, constitutes a very powerful synthetic tool for the formation of dienes. Particular attention has been brought to the application of this methodology to the formation of 1-substituted naphthalenes from 1-tetralone.
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