Effect of Intramolecular Hydrogen Bonding on Thermolysis of Dioxetane: Unusual Instability of Bicyclic Dioxetanes Bearing a Hydroxynaphthyl Group with Vicinal Substitution Pattern

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<jats:title>Abstract</jats:title> <jats:p>Dioxetanes bearing a 1-hydroxynaphthalen-2-yl group 4(OH) or 2-hydroxynaphthalen-1-yl group 5(OH) were found to be significantly unstable thermally in contrast to their methoxynaphthyl-analogs 4(OME) and 5(OME). The marked instability of 4(OH) and 5(OH) was attributed to the intramolecular hydrogen bonding of a hydroxy group on the naphthalene ring.</jats:p>

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  • Chemistry Letters

    Chemistry Letters 36 (4), 516-517, 2007-03-03

    Oxford University Press (OUP)

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