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Crystals 2015, 5(1), 91-99; doi:10.3390/cryst5010091

Synthesis and Reactivity of Novel Boranes Derived from Bulky Salicylaldimines: The Molecular Structure of a Maltolato Compound

1
Department of Chemistry and Biochemistry, Mount Allison University, Sackville NB E4L 1G8, Canada
2
Department of Chemistry, University of New Brunswick, Fredericton NB E3B 5A3, Canada
*
Author to whom correspondence should be addressed.
Academic Editor: Ivana R. Evans
Received: 25 December 2014 / Revised: 12 January 2015 / Accepted: 21 January 2015 / Published: 5 February 2015
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Abstract

Reductive amination of salicylaldehyde or 3,5-di-tert-butylsalicylaldehyde and 1-adamantylamine using NaBH4 gave the corresponding aminoalcohols in high yields. Subsequent addition of one equivalent of H3B·SMe2 to the aminoalcohols, with loss of two equivalents of dihydrogen, resulted in the formation of adamantanyl oxazaborinanes (1a,b). The molecular structure of 1b was studied by a single crystal X-ray diffraction study. Crystals were obtained from a saturated Et2O solution and belong to the triclinic space group Pī with unit cell parameters a = 9.1267(4) Å; b = 11.676(2) Å; c = 12.240(3) Å; α = 66.840(3)°; β = 78.529(3)°; and γ = 67.354(3)°. The molecular structure of the addition product (2a) arising from maltol and 1a was also confirmed by single crystal X-ray diffraction. Crystals were obtained from a saturated 1:2 mixture of toluene/Et2O and belong to the orthorhombic space group Pna2(1) with unit cell parameters a = 18.519(6) Å; b = 17.315(5) Å; and c = 12.680(4) Å. The asymmetric unit contains two molecules that differ slightly in some of the dihedral angles. View Full-Text
Keywords: adamantylamine; adduct; borane; hydroboration; maltol adamantylamine; adduct; borane; hydroboration; maltol
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Bourque, J.L.; Geier, S.J.; Vogels, C.M.; Decken, A.; Westcott, S.A. Synthesis and Reactivity of Novel Boranes Derived from Bulky Salicylaldimines: The Molecular Structure of a Maltolato Compound. Crystals 2015, 5, 91-99.

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