50366-74-0Relevant academic research and scientific papers
Aromatization of 2,2,5-trialkyl-substituted 2,5-dihydrofurans and factors affecting their stabilization
Sharipov, Bulat T.,Davidova, Anna N.,Valeev, Farid A.
, p. 403 - 410 (2018)
[Figure not available: see fulltext.] We demonstrate that the synthesis of 5-methoxy-2,2,5-trialkyl-substituted 2,5-dihydrofurans containing unprotected hydroxymethyl group at the C-2 position involves aromatization via fragmentation involving С–С bond cleavage, resulting in the formation of 2,5-disubstituted furans and carbonyl compounds. 2,5-Dihydrofurans bearing an ester group at the С-2 position were stable. It was found that 2,2,5-trialkyl-substituted 2,5-dihydrofurans containing a hydroxymethyl or carbonyl group in the side chain could aromatize through auto-oxidation, which was facilitated by adjacent functional groups (sulfo- or pivaloyl groups).
