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

Christopher D. Gabbutt, B. Mark Heron, Colin Kilner, Suresh B. Kolla

Research output: Contribution to journalArticle

1 Citation (Scopus)

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.

LanguageEnglish
Pages531-535
Number of pages5
JournalJournal of Chemical Research
Volume35
Issue number9
DOIs
Publication statusPublished - 1 Sep 2011
Externally publishedYes

Fingerprint

Oxocins
Acylation
X ray crystallography
Cyclization
Alkenes
Nuclear magnetic resonance spectroscopy
Esters
Catalysts
2-naphthol
2-hydroxy-1-naphthaldehyde
acryloyl chloride
acrylic acid

Cite this

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title = "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.",
keywords = "1-b]oxocin-5-one, Alkene metathesis, Grubbs' second generation catalyst, Hexatriene, Naphth[2, Wittig reaction",
author = "Gabbutt, {Christopher D.} and Heron, {B. Mark} and Colin Kilner and Kolla, {Suresh B.}",
year = "2011",
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language = "English",
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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; Kolla, Suresh B.

In: Journal of Chemical Research, Vol. 35, No. 9, 01.09.2011, p. 531-535.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Hexatriene formation from the regiospecific alkene cross-metathesis of trans-1-(buta-1,3-dien-1-yl)-2-acryloyloxynaphthalene

AU - Gabbutt, Christopher D.

AU - Heron, B. Mark

AU - Kilner, Colin

AU - Kolla, Suresh B.

PY - 2011/9/1

Y1 - 2011/9/1

N2 - 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.

AB - 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.

KW - 1-b]oxocin-5-one

KW - Alkene metathesis

KW - Grubbs' second generation catalyst

KW - Hexatriene

KW - Naphth[2

KW - Wittig reaction

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M3 - Article

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