63359-63-7Relevant articles and documents
An analysis of substituent effects on 1H and 13C NMR parameters of substituted furans. Linear free energy relationships and PM3 semiempirical calculations
Alvarez-Ibarra, Carlos,Quiroga-Feijoo, Maria L.,Toledano, Emilio
, p. 679 - 689 (2007/10/03)
Forty five furans have been obtained in a synthetic project designed to evaluate monothiosubstituted furans as potential food flavourings. A full NMR (1H and 13C) study and PM3 molecular orbital semiempirical calculations have been carried out. Substituent-induced chemical shifts (SCS) for six and nine substituents at the 2- and 3-positions have been calculated and a separation of inductive and resonance effects of these substituents has been proposed. Finally, a linear correlation between the net atomic charges localized at ring carbons and their 13C NMR chemical shifts has been established.
182. Novel Access to Furan-3-thiols and Derivatives, Impact Meat-Flavor Compounds
Huber, Ulrich A.,Bergamin, Desiree
, p. 2528 - 2536 (2007/10/02)
A versatile process for the preparation of a number of 3-thio-substituted furans 1-4 is described.These products have very low odor thresholds and are thus potent flavor compounds.Fur-3-yl thiocyanates 10a,b as well as other S-containing analogues (2b, 7a, b, and 8) were prepared by a Michael-type addition of thiocyanic acid, thioacetic acid, alkanethiols, and sodium thiosulfate to alkynones 6 and 15, followed by cyclization (Schemes 3 and 4).The thiocyanates 10a, b were converted to mixed disulfides 3, symmetric disulfides 4, thioethers 2, and thiols 1, using 'hard' or 'soft' nucleophiles or reducing agents, respectively (Scheme 6).
