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

Crystals

Jeremy L. Bourque²  Stephen J. Geier²  Christopher M. Vogels²  Andreas Decken¹  Stephen A. Westcott² 

[1] Department of Chemistry, University of New Brunswick, Fredericton NB E3B 5A3, Canada; E-Mail:;Department of Chemistry and Biochemistry, Mount Allison University, Sackville NB E4L 1G8, Canada; E-Mails:

关键词: adamantylamine;    adduct;    borane;    hydroboration;    maltol;   

DOI  :  10.3390/cryst5010091

来源: mdpi

【 摘 要 】

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.

【 授权许可】

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