ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
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Acetone derivates of xylitol and their constitution

F. Valentin and D. Tomkuljak

Slovak Technical University, Bratislava


Abstract: Diacetonexylitol was prepd. and its constitution detd. On treatment with Me2CO and concd. H2SO4, xylitol (I) binds first 1 mol. of Me2CO in a 6-membered heterocycle at positions 3 and 5 of the I mol., forming the amorphous monoacetonexylitol, b0.5 145-7°, nD20 1.4778. Prolonging the reaction time and increasing the amt. of the condensation agent gives diacetonexylitol, in which the 2nd mol. of Me2C is bound at positions 1 and 2 of the sugar mol., forming a 5-membered heterocycle; the amorphous 1,2,3,5-diacetonexylitol b0.5 99-101°, nD20 1.4534. The following derivs. of I were prepd. by oxidation with Pb(OAc)4: 1,2,3,5-diacetone-4-tolylsulfonyl, cryst., m. 71-3°; 3,5-acetone-1,2,4-tribenzoyl, cryst., m. 103-4°; 3,5-acetone-1,2,4-trimethyl, amorphous, b0.5 69-71°, nD20 1.4324; 1,2,4-trimethyl, amorphous, b0.5 97-9°, nD20 1.4510; 1,2,3,5-diacetone-4-methyl, amorphous, b0.5 78-80°, nD20 1.4393; 3,5-acetone-4-methyl, amorphous, b0.5 109-11°, nD20 1.4603; 4-methyl, amorphous, b0.5 167-9°; 1,2,3,5-tetrabenzoyl-4-methyl, cryst., m. 121-2°.

Full paper in Portable Document Format: 35-6a146.pdf (in Slovak)


Chemical Papers 3 (5-6) 146–164 (1949)

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