Degradation eliminative, during methylation

The furanic aldehydes 5-(hydroxy-methyl)furfural and 2-furaldehyde, systematically present in the toasted wood, can be formed by the thermal degradation of 3-deoxyosone during sugar pyrolysis or Maillard reactions (27). They could also be formed from glyceraldehyde, coming from degradation of DDMP, by condensation with subsequent elimination of water or formaldehyde (24). 

Sun and Lovins [212] studied the elimination of neutral fragments, obtained from amino acids liberated during the Edman degradation, which are transformed into derivatives of methyl- (or phenyl-) thiohydantoin (Fig. 59). 

For the other fuel oxygenates detailed studies on the reaction pathways are not as abundantly available in literature. However, the similarity in chemical structure implies similar reaction by-products. In the case of TAME, tert-amyl formate and tert-amyl alcohol were observed instead of fBF and fBA, and their subsequent degradation products however, acetone and methyl acetate were observed as well [117]. The attack on the methoxy group was observed to be the major pathway, corresponding to the MTBE ehmination. During the elimination of ETBE the same reaction by-products were observed as with MTBE, with the exception of fert-butyl acetate which was formed instead of fBF [30]. 

Ciucanu I, Costello CE. Elimination of oxidative degradation during per-O-methylation of carbohydrates. J Am Chem Soc 2003 125 16213-16219. 

I. Ciucanu and E. C. Costello, Elimination of oxidative degradation during the per-O-methylation of earbohydrates, J. Am. Chem. Soc., 125 (2003)... 

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