Synthetic and Structural Investigations On Cyclic Acetals

Yuceer, Levend

(1973)

Yuceer, Levend (1973) Synthetic and Structural Investigations On Cyclic Acetals.

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Abstract

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.

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This is a Accepted version
This version's date is: 1973
This item is not peer reviewed

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https://repository.royalholloway.ac.uk/items/952704b1-cd49-41cc-98b4-8d36ccde0ac7/1/

Item TypeThesis (Doctoral)
TitleSynthetic and Structural Investigations On Cyclic Acetals
AuthorsYuceer, Levend
Uncontrolled KeywordsPhysical Chemistry; Organic Chemistry; Pure Sciences; Pure Sciences; Acetals; Cyclic; Cyclic Acetals; Cyclic Acetals; Investigations; Structural; Synthetic
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Deposited by () on 01-Feb-2017 in Royal Holloway Research Online.Last modified on 03-Feb-2017

Notes

Digitised in partnership with ProQuest, 2015-2016. Institution: University of London, Royal Holloway College (United Kingdom).


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