ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A new, convenient, and safe route to 1,3,5-triamino-1,3,5-trideoxy-cis-inositol (taci) was investigated by hydrogenation of azo-coupled derivatives of phloroglucinol. In the presence of acetic anhydride, the reduction of trisphenylazophloroglucinol (H2/Pd(5%) on C) resulted in the formation of tri-, hexa-, and nona-acetylated derivatives of triaminophloroglucinol. All three compounds are air-stable, colorless solids. However, the succeeding hydrogenation to the cyclohexane derivative failed. Trisodiumtris(p-sulfonatophenylazo)phloroglucinol could be hydrogenated in a one-pot reaction to the desired taci· 1.5H2SO4 using a Pt/Rh oxide as catalyst. taci provides two distinct chair conformations with either three amino or three hydroxy groups for metal binding. The unique metal-binding properties are discussed in terms of minimal conformational changes required for coordination. Conformational analysis, based on X-ray structural data of [BiCl6][H3(taci)] ·2 H2O (Pnma, a = 24.314 (5) Å, b = 10.215 (2) Å, c = 7.422 (8) Å, R = 5.8%) and [Co(taci)2(NO3)3]·2H2O (C2/c, a = 22.912 (8) Å, b = 8.942 (2) Å, c = 14.731 (3) Å, β = 128.66 (2)°, R = 4.9%) and the previously investigated [Cr(taci)2]3+ revealed an almost ideal chair conformation in all three molecules.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19920750709
