according pg 468 of March's 5ht ed, 2,5-dimethylfuran reacted with H2SO4 and H2O gives 1,4-hexadione. Following this, it looks like plain old furan would give the 1,4 aldehyde ?
Dont know this ref. Did they seperate this produkt or did they only found it spectroscopically?
Yields?
Perhaps the Methyl-groups are the key? M ; I effekt
From where is all the hydrogen ?
THF under this conditions will give peroxides......booom.
But the thought seems to be interesting.
I ll try it.
2,5-dimethoxytetrahydrofuran (a cyclic acetal) can be hydrolyzed by acid to succindialdehyde, acid cleavage of THF would only yield butandiol derivatives. UTFSE.
Also see
Post 458701 (https://www.thevespiary.org/talk/index.php?topic=9211.msg45870100#msg45870100)
(Rhodium: "2,5-Dimethoxy-tetrahydrofuran from Furan", Methods Discourse)
furan -ch2-ch2-ch2-c2-o-, a saturated ether, cleaved would produce butanediol, but wouldn't tetrahydrofuran, -ch=ch-ch=ch-o-, an unsaturated ether, when cleaved produce initally a vinyl alcohol which would isomerize to the aldehyde?
You have confused the structure of furan and tetrahydrofuran.
what i read was the unsaturated one, the one with the double bonds, when cleaved with acid at elevated temperatures in the presence of water forms succindialdehyde which under these conditions polymerizes explosively. when cleaved with acid at elevated temperatures in the presence of alcohol it forms succindialdehydyde diacetal which under these conditions is stable and does not react further.