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6. Striking difference in reactivity of trienes and oximes derived from glucose and xylose.

Author

Jaźwinski, Jarosław, Łata, Paweł, Tiara, Karolina, and Jarosz, Sławomir

Subjects
*TRIENES, *XYLOSE, *GLUCOSE, *MOLECULAR orbitals, *RING formation (Chemistry)
Abstract

D-Glucose was converted into a dieno-oxime and independently into a triene. Both derivatives were completely unreactive and did not undergo any cyclization: either [1,3]-dipolar cycloaddition (oxime) or [4+2] cycloaddition (triene). This result was very surprising comparing to similar examples observed by us for derivatives of 'shorter' sugar: D-xylose. The big difference in reactivity of the pentose and hexose derivatives is clarified by an in silico study. [ABSTRACT FROM AUTHOR]

Published
2021
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