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Converting dipyrrinones to lactim ethers to fluorescent N,N′-difluoroboryl derivatives

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Abstract

A high-yield straightforward conversion of lactams to lactim ethers is shown by the conversion of (10H)-dipyrrin-1-ones to (11H)-dipyrrin-1-ol methyl and ethyl ethers in 90% yield from heating in neat trimethyl or triethyl phosphite at 160°C. Unlike the parent dipyrrinones, which form intermolecularly hydrogen-bonded dimers in CHCl3, their lactim ethers are shown to be monomeric by vapor pressure osmometry. The latter react with boron trifluoride etherate to N,N′-bridged BF2 derivatives that exhibit strong fluorescence (φF 0.6–0.8) near 535 nm. X-Ray crystal structures were obtained of the lactim ethyl ether of kryptopyrromethenone and the BF2 derivative of the lactim ethyl ether 2,3-diethyl-7,8-dimethyl-(10H)-dipyrrin-1-one.

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Authors and Affiliations

  1. Department of Chemistry, University of Nevada, Reno, Nevada, USA

    Suchitra Datta & David A. Lightner

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  1. Suchitra Datta
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  2. David A. Lightner
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Correspondence to David A. Lightner.

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Correspondence: David A. Lightner, Department of Chemistry, University of Nevada, Reno, Nevada 89557-0020 USA.

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Datta, S., Lightner, D. Converting dipyrrinones to lactim ethers to fluorescent N,N′-difluoroboryl derivatives. Monatsh Chem 139, 1519–1529 (2008). https://doi.org/10.1007/s00706-008-0943-z

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  • DOI: https://doi.org/10.1007/s00706-008-0943-z

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