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Hexatriene formation from the regiospecific alkene cross-metathesis of trans-1-(buta-1,3-dien-1-yl)-2-acryloyloxynaphthalene

Gabbutt, Christopher D., Heron, B. Mark, Kilner, Colin and Kolla, Suresh B. (2011) Hexatriene formation from the regiospecific alkene cross-metathesis of trans-1-(buta-1,3-dien-1-yl)-2-acryloyloxynaphthalene. Journal of chemical research, 35 (9). pp. 531-535. ISSN 1747-5198

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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 1 H NMR spectroscopy and by X-ray crystallography.

Item Type: Article
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Sharon Beastall
Date Deposited: 18 Sep 2012 11:25
Last Modified: 28 Aug 2021 11:21


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