Article ID Journal Published Year Pages File Type
1197687 Journal of Analytical and Applied Pyrolysis 2008 28 Pages PDF
Abstract

The flash pyrolysis of d-glucose was investigated by the use of 13C labeling, in conjunction with GC/MS. Co-pyrolysis of uniformly labeled and unlabeled d-glucose established the extent of unimolecular formation of each of the pyrolysis products. A complete set of singly labeled d-glucose isotopologs was used to determine the origin of specific carbons within each of the pyrolysis products. The results were compared with the expected labeling patterns that arise when the cyclic Grob 1,3-diol fragmentation and the tandem alkaline pinacol rearrangement/retro-aldol fragmentation (TAPRRAF) discovered from the pyrolysis of glycerin are used to initiate breakage of the six-carbon chain of d-glucose. The most promising rationalizations provided by this exercise are presented herein, for the formation of six C3 and eight C4 acyclic carbonyl-containing pyrolysis products, and for 3-cyclopentene-1,2-dione.

Related Topics
Physical Sciences and Engineering Chemistry Analytical Chemistry
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