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UBC Theses and Dissertations

The structures and conformations of some cyclic 0-benzylidene acetals of hexitols Conder, David W.


The structure of the previously reported di-0-benzylidene acetal of allitol has been established as that of 2,4;3,5-di-0-benzylidene allitol. An infrared spectroscopic study in carbon tetrachloride solution of the intramolecular hydrogen bonding existing in this compound and the related diacetal, 1,3;4,6-di-0-benzylidene dulcitol was made to determine the preferred molecular conformations. An intraring, bifurcated hydrogen bonded conformation was assigned to the dulcitol derivative. For the allitol derivative no final decision could be made on the basis of existing evidence between the two possible intramolecularly hydrogen bonded conformations. A spectroscopic method for the determination of the number of cyclic 0-benzylidene groups present per mole of parent alcohol has been developed.

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