76826-32-9

Upstream product

• 930-69-8 sodium thiophenolate 
• 76827-73-1 (2Z,4Z)-2,3,4,5-Tetrachlor-2,4-pentadienthiosaeure-S-phenylester 
• 76826-29-4 Z,Z-2,4,5-Trichlor-3-phenylthio-2,4-pentadienoylchlorid 
• 80674-06-2 (2Z)-2,4,5-Trichlor-3,5-bis(phenylthio)-2,4-pentadienal 

Downstream Products

• 77118-77-5 Z,Z-2,4-Dichlor-3,5-bis(phenylthio)-2,4-pentadienthiosaeure-S-phenylester 

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.

Umlagerungen vinyloger Carbonsaeurechloride, XXVIII. 1,5-Pentadien-Sauerstoffverschiebung von Z-2,2,5,5-Tetrachlor-3-arylthio-2,4-pentadienalen

Nucleophilic substitution on C-3 occurs, when the aldehyd 1 is treated with aryl thiolates in ethanol at 0 deg C.The structure and configuration of the products 2 is confirmed by thermal rearrangement of 2a to the acyl chloride 3a, which is converted into

Umlagerungen vinyloger Carbonsaeurechloride, XXVII. Darstellung und thermisches Verhalten von chlor- und organylthiosubstituierten Z,Z-2,4-Pentadienthiosaeure-S-estern

The title compounds 2 are attacked at room temperature by thiolates in ethanol at C-3 giving 6 and free thiols in boiling carbon tetrachloride at C-5 yielding 11.For the former reaction nucleophilic displacement directly at C-3 of 2, for letter at C-2 of the pyran intermediate 3 is assumed.With respect to the different reaction conditions the dithio substituted esters 10 are available from 6 as well as from 11.The structures of 6 and 11 are confirmed by 13C-NMR spectra.On heating the Z,Z-ester 6b at 80 deg C an equilibrium with the Z,E-ester 9b is evolved via the pyran stage 5b.In contrast to this reaction the Z,Z-ester 11b is therm ally stable.