Acidity thiols

Thiol acids and thiol esters can be prepared in this manner, which is analogous to 10-8 and 10-24. Anhydrides and aryl esters (RCOOAr) are also used as substrates, but the reagents in these cases are usually SH and SR. Thiol esters can... 

Alcohols, when treated with a thiol acid and zinc iodide, give thiol esters (R COSR). ... 

Acid derivatives that can be converted to amides include thiol acids (RCOSH), thiol esters (RCOSR), ° acyloxyboranes [RCOB(OR )2]. silicic esters [(RCOO)4Si], 1,1,1-trihalo ketones (RCOCXa), a-keto nitriles, acyl azides, and non-enolizable ketones (see the Haller-Bauer reaction 12-31). A polymer-bound acyl derivative was converted to an amide using tributylvinyl tin, trifluoroacetic acid, AsPh3, and a palladium catalyst. The source of amine in this reaction was the polymer itself, which was an amide resin. 

Addition of thiol acids to alkenes addition of thiols to ketenes... 

Preparation Of Thiol Acids, Thiol Esters And Amides By Reactions Of Carbonyl Sulfides With Grignard Reagents," Katritzky. A.R. Moutou, J.-L. Yang, Z. Org. Prep. Proceed. Int., 1995, 27, 361... 

Diastereoselective conjugate addition of oxygen and nitrogen- centered nucleophiles to nitroalke-nes derived from (+)-camphoisulfonic acid and ozonolysis give a-hydroxy and a-amino thiol acid derivatives (Eq. 4.39). In all cases, the (/ )-diasteromer is formed as the major component.49... 

Sidky, M.M., Soliman, F.M., and Shabana, R., Organophosphorus compounds. XIV. Reaction of dialkyl phosphites and thiol acids with 4-benzylidene-l,2-diphenyl-3,5-pyrazolidinedione, Egypt. J. Chem., 15, 79, 1972. 

Schubert M. 1932. Complex types involved in the catalytic oxidation of thiol acids. J Am Chem Soc 54 4077-85. 

JO-C6H4CO2BUO, followed by ozonolysis, gave the a-hydroxy and a-aimno thiol acid derivatives (140). In all cases, the (l )-diastereoisomer was formed as the major component albeit with only modest levels of selectivity (33-71% de)P... 

The S—H group of thiol acids absorbs in the same region as mercaptans and thiophenols. 

Acid derivatives that can be converted to amides include thiol acids RCOSH, thiol esters RCOSR,911 acyloxyboranes RCOB(OR )2,912 silicic esters (RCOO)4Si, 1,1,1-trihalo ketones RCOCX3,913 a-keto nitriles, acyl azides, and nonenolizable ketones (see the Haller-Bauer reaction 2-33). 

From thiol acids and a-halo ketones Thiols... 

Hydroxy and 7-thiol acids (32 Z = 0, S) usually cyclize spontaneously to give lactones and thiolactones (33). 7-Amino acids (32 Z=NH) require heating to effect lactam formation (33 Z = NH). 

Thiol acids, esters, lactones N-Phenylselenophthalimide, 245 Zirconium(IV) acetylacetonate, 351... 

Boc amino acid thioesters 7 used in Boc-SPPS are prepared by reaction of Boc amino acid active esters such as the 4-nitrophenyl ester (ONp) or succinimide ester 6 (OSu) with thiols containing a carboxy group that can link to a resin (Scheme 3, Table 2). 1314 Amino acid thioesters 7 can also be prepared by reaction of Boc amino thiol acids 8 with a chloro, bromo, or hydroxy compound that also contains a carboxy group (Scheme 3, Table 2). 1516 ... 

Pyrrolidine (39 Z = NH) and thiolane (39 Z = S) can be prepared from tetramethylene dibromide 38, and tetrahy-drofuran (39 Z = O) is obtained from the diol 40. -Hydroxy and -thiol acids (41 Z = O, S) usually cyclize spontaneously to give lactones and thiolactones 42. -Amino acids (41 Z = NH) require heating to effect lactam formation (42 Z = NH) (Scheme 31). 

Afurther method ia by the reaction of ethyl or Mobutylehlorofbmatv with a J -thiol acid with 2 molar equivalMits of tdothylamine. - The reaction is run in chloroform first at -10 to —6% then at rouu] toinperatuio. The authors aaiume that a raized anhydride inter-... 

D. KoBctioD of on A] Chloroformato with A/3-Thiol Acid . Attempt to oombiiie KeteoM with Tbioketonee... 

The nucleophiles ranged from fluoride ion to alcohols, thiols, acids, and cyanide ion. This oxaziridine is unique in having a good leaving group on carbon. 

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