Issue 4, 1992
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Through-bond modulation of N→B ring formation shown by NMR and X-ray diffraction studies of borate derivatives of pyridyl alcohols

Norberto Farfán,   Dolores Castillo,   Pedro Joseph-Nathan,   Rosalinda Contreras  and  László v. Szentpály  

Abstract

The preparation of diphenyl(2-pyridylmethoxy-O,N)borane (2a), diphenyl[1-(2-pyridyl)ethoxy-O,N]borane (2b), diphenyl[α-(2-pyridylbenzyloxy-O,N)]borane (2c), diphenyl[2-(2-pyridyl)ethoxy-O,N]borane (4), benzene-1,2-diyldioxy(2-pyridylmethoxy-O,N)borane (5) and benzene-1,2-diyldioxy[2-(2-pyridyl)ethoxy-O,N]borane (6) is reported. The cyclic structures 2a and 4 were established by X-ray diffraction studies, the N→B bond distance being 1.642 Å for 2a and 1.685 Å for 4. Complete assignment of the 1H and 13C NMR spectra of 2a–c and 4 was achieved from two dimensional HETCOR data. Additional evidence for the strength of the five- and six-membered rings in boron esters was obtained from variable-temperature measurements which show partial ring opening for the six-membered ring compounds at 180 °C. The observation that five-membered rings are more stable than six-membered ones is attributed to sigma-assistance by through-bond interactions.

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Article information

DOI
https://doi.org/10.1039/P29920000527
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1992, 527-532

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Through-bond modulation of N→B ring formation shown by NMR and X-ray diffraction studies of borate derivatives of pyridyl alcohols

N. Farfán, D. Castillo, P. Joseph-Nathan, R. Contreras and L. v. Szentpály, J. Chem. Soc., Perkin Trans. 2, 1992, 527 DOI: 10.1039/P29920000527

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