Chlorolysis of 1,2-dithiolan-3-ones,1,2-dithiol-4-en-3-ones, and acetyl alkyl disulfides
The direction of the chlorolysis of acyl alkyl disulfides depends on the character of the alkyl radical, and can go with a cleavage of the S-S bond, the S-CO bond, or with a simultaneous cleavage of both bonds. The probability of cleaving the S-CO bond increases with increase in the electronegativity of the alkyl radical.
The chlorolysis of 1,2-dithiolan-3-ones and 1,2-dithiol-4-en-3-ones by SO2Cl2 goes in an unambiguous manner, with a cleavage of the S-CO bond and the formation of heat stable acid chlorides ofβ-(chlorodisulfenyl)carboxylic acids.
The presence of electron-withdrawing substituents in both cyclic and open acyl alkyl disulfides hinders the chlorolysis.
KeywordsChloride Disulfide Carboxylic Acid Acetyl Alkyl Radical
Unable to display preview. Download preview PDF.
- 1.T. P. Vasil'eva, M. G. Lin'kova, O. V. Kil'disheva, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 2379 (1973); 700 (1974).Google Scholar
- 2.F. Boberg, Angew. Chem.,73, 579 (1961).Google Scholar
- 3.H. Böhme and G. Ham, Ann. Chem.,617, 62 (1958).Google Scholar
- 4.T. P. Vasil'eva, M. G. Lin'kova, O. V. Kil'disheva, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim., 209 (1973).Google Scholar