Synthesis and Reactivity of Novel Boranes Derivedfrom Bulky Salicylaldimines: The Molecular Structure ofa Maltolato Compound

Crystals

Jeremy L. Bourque¹  Stephen J. Geier¹  Christopher M. Vogels¹  Stephen A. Westcott¹  Andreas Decken² 

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

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

DOI  :  10.3390/cryst5010091

来源: DOAJ

【 摘 要 】

Reductive amination of salicylaldehyde or 3,5-di-tert-butylsalicylaldehyde and1-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 spacegroup 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】

Unknown