74725-08-9Relevant academic research and scientific papers
ACTIVATION OF CARBOXYL GROUPS BY DIPHENYL 2-OXO-3-OXAZOLINYLPHOSPHONATE. FACILE PREPARATION OF VERSATILE REAGENTS, 3-ACYL-2-OXAZOLONES
Kunieda, Takehisa,Higuchi, Tsunehiko,Abe, Yoshihiro,Hirobe, Masaaki
, p. 3253 - 3260 (2007/10/02)
Synthetic utility of the 2-oxazolone moiety as an excellent new leaving group is described.Based on such a function of the heterocycles, diphenyl 2-oxo-3-oxazolinylphosphonate has been newly introduced as a carboxyl-activating reagent which permits a facile direct preparation of 3-acyl-2-oxazolones and amides including peptides from a wide variety of carboxylic acids.The 3-acyl-2-oxazolides also serve as versatile reactive agents for highly chemoselective acyl-transfer to the nucleophilic species such as amines, alcohols and thiols, providing convenient and high-yield routes to amides, esters and thiol esters under mild conditions.They are also useful intermediates for ketones and alcohols.
EFFICIENT CONVERSION OF CARBOXYLIC ACIDS INTO THIOL ESTERS
Kunieda, Takehisa,Abe, Yoshihiro,Hirobe, Masaaki
, p. 1427 - 1428 (2007/10/02)
A facile and direct preparation of thiol esters from carboxylic acids and thiols using diphenyl 2-oxo-3-oxazolinylphosphonate in the presence of triethylamine is described.
A FACILE PREPARATION OF THIOL ESTERS FROM CARBOXYLIC ACIDS AND THIOLS
Kim, Sunggak,Yang, Sungbong
, p. 133 - 134 (2007/10/02)
Thiol esters can be conveniently prepared by the reaction of carboxylic acids with thiols and 1-fluoro-2,4,6-trinitrobenzene in the presence of 4-dimethylaminopyridine.The thiol ester formation is found to be very effective for simple carboxylic acids.
Studies on the Reaction of 3,3,4,4-Tetraphenylthietan-2-one
Charumilind, P.,Kohn, Harold
, p. 4359 - 4365 (2007/10/02)
The chemical reactivity of 3,3,4,4-tetraphenylthietan-2-one (3,3,4,4-tetraphenyl-β-thiolactone, 5) toward nucleophilic, reducing, and oxidizing reagents has been investigated.Compound 5 is relatively inert toward nucleophiles (1-butanethiol, sodium hydroxide, sodium methoxide).The only product obtained from these reactions which cannot be readily attributed to initial thermal fragmentation of the ring is tetraphenylethylene (10).Treatment of 5 with the strong reducing reagent LiAlH4 gave four products upon workup: 2,2,3,3-tetraphenyl-1-propanol (19), 2,2,3,3-tetraphenylpropyl acetate (20), 1,1,3,3-tetraphenyl-2-propanone (7), and 1,1,3-triphenyl-2-indanone (21).The substituted acetone 7 was also obtained when DIBAL was added to 5.Desulfurization experiments with Raney nickel and cobalt catalysts consistently gave 10 in varying amounts.In addition to the alkene 10, compounds 7, 21, and 2,2,3-triphenyl-4,5,6,7-tetrahydro-1-indanone (26) were also isolated with W-2 Raney nickel.Finally, oxidation of 5 with m-chloroperbenzoic acid gave the novel mixed carboxylic-sulfinic acid anhydride (32).This molecule is of particular interest in light of the previous difficulty encountered in the preparation of this class of compounds.Many of the products obtained in these reactions are not those expected based upon previous studies of β-thiolactones.Potential pathways for the origin of the compounds obtained are suggested.
