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Title: Synthetic and structural investigations on cyclic acetals
Author: Yuceer, Levend
Awarding Body: University of London
Current Institution: Royal Holloway, University of London
Date of Award: 1973
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I. Acid catalysed formation of butylidene acetals of certain polyols and D-galactose was studied. i) Galactitol afforded the 1,3-O-butylidene and 2,3- O-butylidene monoacetals without any kinetically controlled product. ii) 1-Deoxy-B-galactitol (L-fucitol) produced 4,6-O-butylidene-1-deoxy- D-galactitol as main product together with a stereoisomeric mixture of 2,3-monoacetals and a pure 4,5-monoacetal. iii) Galactitol under stronger conditions initially produced a complex mixture from which was isolated 2,3:4,5-di-O-butylidene acetal and another dibutylidene acetal with the probable structure of 2,4:5,6-di- O-butylidene acetal in small yields and 1,3:2,4:5,6 tri- O-butylidene-DL-galactitol and 1,3:4,6-di- O-butylidenegalactitol in moderate yields. Longer reaction times afforded the 1,3:4,6-di-O-butylidene-galactitol as the main product with a considerable amount of 1,3:2,4:5,6-triacetal. iv) 3-O-Methyl-D-glucitol afforded a stereoisomeric mixture of 2,4;5,6-di-O-butylideneacetal as the only diacetal. v) 1-Deoxy-D-glucitol gave the 2,4:5,6-di-O -butylidene derivative as the main diacetal. vi) 2-Deoxy-D-glucitol gave an unidentified kinetically controlled product and 1,3:4,6-di-O-butylideneacetal as the thermodynamically controlled diacetal. vii) D-Galactose afforded the 4,6-O-butylidene derivative as the main monoacetal. II. A new method for separating the five and six-membered cyclic acetals of polyols on basic resin Dowex-1 x 8 (OH-) is described. III. Nuclear magnetic resonance spectroscopy and mass spectrometry were used for characterisations and structural analysis of the butylidene acetals. IV. The possibility of utilization of JH-C-OH type vicinal coupling constants in deriving structural information about cyclic acetals is discussed.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Physical Chemistry