533889-38-2

Upstream product

• 870-63-3 prenyl bromide 
• 404825-83-8 isopropyl {[3,5-bis(trifluoromethyl)phenyl]sulfonyl}acetate 
• 29921-57-1 isopropyl 2-bromoacetate 
• 130783-02-7 3,5-bis(trifluoromethyl)thiophenol 
• 533888-83-4 isopropyl {[3,5-bis(trifluoromethyl)phenyl]thio}acetate 

Relevant academic research and scientific papers

Synthesis and reactivity of π-electron-deficient (arylsulfonyl)acetates

Different π-electron-deficient (arylsulfonyl)acetates 9 were synthesized (Scheme 1, Table 1), and their behavior as soft nucleophiles in the dialkylation reaction under phase-transfer catalysis conditions was studied (Schemes 2 and 3, Tables 2 and 3). The [3,5-bis(trifluoromethyl)phenyl]sulfonyl group was shown to be the best substituent for the stereoselective synthesis of (E)-aconitates 18 via an alkylation hydro-sulfonyl-elimination integrated process under very mild phase-transfer-catalysis conditions (Scheme 5, Table 4). Sulfonylacetates 9h,i also underwent smooth Diels-Alder reactions with acyclic and cyclic dienes via in situ formation of the appropriate dienophile through a Knoevenagel condensation with paraformaldehyde (Scheme 6). Reductive desulfonylation with Zn and NH4Cl in THF was shown to be an efficient method for removal of the synthetically useful sulfonyl moiety (Scheme 7).

Replacement of imine fragment in the ring of 2,6-disubstituted 1,4,3,5-octathiadiazine-4,4-dioxides in reaction with cyano-containing compounds

Reactions of 2,6-disubstituted 1,4,3,5-octathiadiazine-4,4-dioxides with cyano-containing compounds (nitriles, thiocyanates, N,N-disubstituted cyanamides) proceeding with replacement of imine fragment in dioxide by corresponding fragment of cyanide were investigated. The limits of the reaction were revealed determined by electronic effects of substituents R1 and R2 in dioxide and R3 in cyanide. Transimination occurred in dioxides with strong electron-withdrawing substituents R 1 (CCl3, CBr3, C6F5)and weak acceptor or donor substituents R2 (4-NO2C 6H4, 4-ClC6H4, CH3) under the action of compounds R3C≡N with cyano groups of relatively high nucleophilicity (R3 = 4-ClC6H 4, C6H5, (CH3)2CHS, piperidino, morpholino, diethylamino), on the one hand, and with strong electron-withdrawing substituents R3 (CCl3) on the other hand.