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Conformational effects on the mechanism of acid-catalyzed dehydration of hexitols

✍ Scribed by Lj. Došen-Mićović; Ž. Čeković

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
94 KB
Volume
11
Category
Article
ISSN
0894-3230

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✦ Synopsis

The Monte Carlo search of the low-energy regions of D-mannitol (4) and D-glucitol (5) conformational space was undertaken in order to investigate conformational effects on the stereochemistry of the acid-catalyzed dehydrative cyclization reaction of 4 and 5 to the corresponding 1,4:3,6-dianhydrohexitols. It was found that although dominant conformations in water resemble closely the crystal state conformations of 4 and 5, the same is not true in solvents of low polarity. The magnitudes of the calculated energies of the reactive conformations for the dehydrative cyclization reaction suggest an S N 2 mechanism with a late transition state.

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