Hexatriene Formation from the Regiospecific Alkene Cross-Metathesis of Trans-1-(Buta-1,3-Dien-1-yl)-2-Acryloyloxynaphthalene

Abstract

Wittig olefination of 2-hydroxy-1-naphthaldehyde with allylidenetriphenylphosphorane afforded trans-1-(buta-1,3-dien-1-yl)-2-naphthol in good yield. Subsequent O-acylation with acryloyl chloride provided the corresponding acrylate ester. Attempts to effect cyclisation of the latter by ring-closing metathesis with Grubbs’ 2nd generation catalyst failed to provide 5H-naphth[2,1-b]oxocin-5-one and instead induced a novel cross-metathesis reaction to generate trans,trans,trans-1,6-bis(2-acryloyloxynaphthalen-1-yl)hexa-1,3,5-triene, the structure of which was established by ¹H NMR spectroscopy and by X-ray crystallography.