2- Methylfuran. decomposition

Reaction of cis-2,3-bis(trimethylsilyl)cyclopropanone with p-ketophosphorus ylide gives 2-trimethylsilyl-3-trimethylsilylmethyl-5-methylfuran and 2-methyl-4-trimethyl-silylmethylfuran in a ratio of 77 23 <00TL3399>. y-Hydroxyketal 72 undergoes acidic decomposition to afford the corresponding furan derivatives <00CEJ2887>. 

The great instability of 2-bromomethyl- and 2-chloromethyl-furans, often manifest as violent or explosive decomposition on attempted distillation, is reviewed. The furan nucleus is sensitive to traces of halogen acids, and decomposition becomes autocatalytic. Individually indexed compounds are 2,5-Bis(chloromethyl)thiophene, 2305 2-Bromomethylfuran, 1840 2-Bromomethyl-5-methylfuran, 2346... 

Fig. 5 shows the rate of production of volatile compounds from starch and from D-glucose. It is apparent that furan and 2-methylfuran are initially produced in largest proportion, although this is not true of the summative yields in Table V. Again, although the total yields of acetaldehyde and acetone are each comparable to those of the furans, the initial rate of production is much less, but it does not decrease so much with time. These observations suggested that furan and its derivatives may be the primary decomposition products this hypothesis is discussed on p. 506. 

A reverse Diels-Alder reaction, the decomposition of 2-methylfuran-maleic anhydride ejro-adduct (in iso-octane) was the object of an extensive study of isotope effects . Here rehybridisation is from ip to sp and therefore a ratio knlko > 1 is to be anticipated. This has, in fact, been found (/ h/ d)50 c = 108 per D atom, both for all possible deuterations on the maleic anhydride moiety (see below), either at X or at Y or at X and at Y, and for deuteration of the furan moiety at Z. 

Lifshitz A, Tamburu C, Shashua R. Decomposition of 2-methylfuran. Experimental and modeling study. / Phys Chem A. 1997 101 1018-1029. 

Davis AC, Sarathy SM. Computational study of the combustion and atmospheric decomposition of 2-methylfuran. J Phys Chem A. 2013 117 7670-7685. 

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