77118-74-2

Downstream Products

• 77118-73-1 Z,Z-2,3,4-Trichlor-5-(4-methylphenylthio)-2,4-pentadienthiosaeure-S-(4-methylphenylester) 
• 77118-79-7 Z,Z-2,4-Dichlor-3,5-bis(4-methylphenylthio)-2,4-pentadienthiosaeure-S-(4-methylphenylester) 
• 80674-10-8 3,5-Dichlor-2-(4-methylphenylthio)-4H-pyran-4-on 

Relevant academic research and scientific papers

Umlagerungen vinyloger Carbonsaeurechloride, XXX. Thermische Umlagerungen von chlor- und organylthiosubstituierten (2Z,4Z)-2,4-Pentadienalen und -onen zu (2Z,4Z)-2,4-Pentadienthiosaeure-S-estern

The pentadienals 2 are prepared by reduction of the corresponding acyl chlorides 1.The ketone 2d is synthesized from 1b with lithium tert-butyl(phenylthio)cuprate.Elimination of methyl chloride and cyclization occurs on treatment of 1a with AlCl3 giving the 2H-thiopyran-2-one 8.In boiling carbontetrachloride the aldehydes 2 rearrange by 1,5-chlorine shift completely and stereospecifically into the thiolates 3.The analogous reaction 2d -> 3d is non stereospecific.As expected, compounds 2 and 3 may be converted into the same 4H-pyran-4-ones 6.The rearrangement 2 -> 3 is accelerated by RS-groups instead of chlorine in the 5-position and decelerated in the 3-position.The substituent influences and the reaction mechanism are discussed.