Diacyl disulfide

One alternative to the silver ion catalyzed coupling reaction of thiocarboxy C-terminus peptides uses acyl disulfides as the activated species.The thiocarboxy group of 17 reacts with the diaryl disulfide 18 to give an unsymmetrical acyl disulfide 19 in DMF and a symmetrical diacyl disulfide 20 in aqueous DMF. Both acyl disulfides react with the a-amino group of another segment to form the desired peptide bond (Scheme 7). 

When chlorine reacts with diacyl disulfides it is not the disulfide link that is broken but a carbon-sulfur bond, and l-acyl-2-disulfanes are formed 649... 

Oxidation of Se-phenyl selenothioates 31 (R=i-Pr, Bu, Tol) with m-CPBA in ether gave a mixture of E- and Z-S-oxides (sulfines) 66, phenylseleno acyl sulfides 67, diphenyl diselenide, and diacyl disulfides 68 (only in the case of R=Tol) (Eq. 17) [12]. It was proposed that compounds 67 were formed by rearrangements of oxathiirane intermediates 69 [12]. 

SOCI2) underwent conversion to 147 water and the symmetrical diacyl disulfide RCOSSCOR were liberated in the process. Initial formation of an acyl sulfinyl thioanhydride, 163, immediately suffering S-S cleavage from the second molecule of the thioacid, has been suggested [102] the sulfenic acid (formula 109) liberated by this reaction would react with the third thioacid equivalent to yield the observed product. Obtained disulfides 147 were then desulfurized with PPhj to thioesters 127 [55, 93], as described in the previous paragraph. 

Like diacyl peroxides, diacyl disulfides are desulfurized (90) readily by phosphines. 

Diacylamines, mixed s. N-Acyl-carboxylic acid amides C-Diacylation, mixed 17,879 suppl. 26 Diacyl disulfides... 

Oxidative Coupling of Ifrthiols with Diacyl Disulfides. 106... 

Oxidative Coupling of Dithiols with Diacyl Disulfides... 

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