88790-06-1

Upstream product

• 155444-61-4 phenyl β-(trifluoromethyl)vinyl sulfide 
• 100-68-5 methyl-phenyl-thioether 
• 34509-09-6 1,1,1-trifluoro-3-(phenylthio)propan-2-one 
• 88790-04-9 2-hydroxy-3,3,3-trifluoropropyl phenyl sulfide 
• 88790-05-0 Methanesulfonic acid 2,2,2-trifluoro-1-phenylsulfanylmethyl-ethyl ester 
• 108-98-5 thiophenol 

Downstream Products

• 177272-50-3 1-Bromo-1-phenylsulfanyl-3,3,3-trifluoroprop-1-ene 

Relevant academic research and scientific papers

Diels-Alder reaction of 1-phenylsulfonyl-3,3,3-trifluoropropyne with 1,3-dienes

1-Phenylsulfonyl-3,3,3-trifluoropropyne, prepared in situ from 1-phenylsulfonyl-2-bromo-3,3,3-trifluoropropene and triethylamine, reacted with 1,3-dienes to give the cycloadducts and/or 2-trifluoromethyl phenylsulfone in good to excellent yield.

2-HALOVINYL ARYL SULFONES: NEW COUPLING REAGENTS FOR CARBOXAMIDE FORMATION

E-2-Chlorovinyl p-nitrophenyl sulfone 6 and 2-bromo-2-trifluoromethylvinyl phenyl sulfone 7a reacted with carboxylic acids in the presence of a molar equiv of Et3N affording the corresponding 2-acyloxyvinyl sulfones 8, 11, 17, 18, 22, 25, 28 and 29.The latter, on treatment with amines, gave amides 9, 13, 19, 23 and 26 and peptides 30 and 32.These reagents 6 and 7a were also used for the formation of N-methylanilides 13d, 13e, 19d, 23 and 26.Particularly, 6 was successfully used for synthesis of a macrocyclic lactam 23 involving a N-methylanilide moiety.The amidation reac tions proceeded under essentially neutral conditions.Therefore, base-sensitive β-hydroxycarboxy-N-methylanilides such as 26, whose structural unit was involved in maytansine 5, could be prepared by the present method.The reagent 6 was also effective for the preparation of peptides such as Val-N-MeVal derivatives (e.g.32), which were difficult to prepare by other methods.