33500-20-8Relevant articles and documents
Surprising reaction of 5-(phenylthio)- and 5-(methylthio)pent-2-en-4- inal with HCl
Bacilieri, Christian,Neuenschwander, Markus
, p. 1191 - 1199 (2007/10/03)
Contrary to expectations (Scheme 1), 5-(phenylthio)-(1a) as well as 5- (methylthio)pent-2-en-4-inal (1b) react with a slight excess of HCl to give 2-[bis(phenylthio)mcthyl]furan (17a, 77% yield) and 2- [bis(methylthio)methyl]furan (17b, 61% yield), respectively. Structures 17a and 17b are supported by the results of an X-ray crystal-structure analysis, by spectroscopic data in comparison to those of model compounds, and by synthesis of 17a. This surprising reaction is tentatively explained by a mechanism (Scheme 4), including a special pyran → furan ring-contraction sequence, which is in agreement with a labelling experiment.