82172-06-3Relevant academic research and scientific papers
Rearrangements of Vinylogous Acyl Chlorides, XXXI. - 1,5-Pentadiene-Oxygen Transfer of S-Phenyl (Z)-2,3,5,5-Tetrachloro-4-phenylthio-2,4-pentadienethioate and (Z)-2,3,5,5-Tetrachloro-4-phenylthio-2,4-pentadienal
Roedig, Alfred,Fleischmann, Klaus
, p. 675 - 682 (2007/10/02)
SN2'-reaction of the perchloro-substituted acid 1 with thiolates yields the stereoisomeric pentadienoic acids 3.Z-3a gives ring closure to the pyrone 4a at 180 degC, while E-3a is unchanged.The mixture Z/E-3a is converted into the thioates Z- and E-6a as well as into the aldehydes Z- and E-12a.In boiling tetrachlormethane Z-6a and Z-12a rearrange into the acyl chlorides 10a and 14a, respectively.E-6a is stable up to 250 degC.Z-12a in acetic acid gives the pyrone 11a, whereas E-12a does not react.
