S-Ethyl Ethanethiosulfinate

Stabilized Sulfur Ylides. Treatment of methacryloyl Isocyanate with ESDA gave the corresponding carbamoyl yllde (eq 20). 

Related Reagents. Two similar carbonyl-stabilized dimethyl-sulfonium methylides (1 and 2) have been reported to function as cyclopropanating reagents In a fashion analogous to 

Suzuki, K. Aoki, S.-L Okamura, K. Yamashlta, M. Takahashi, L Tanaka, T, Chem. Pharm. Bull. 1986, 34, 4939. 

Modern Synthetic Reactions, 2nd ed. Bergamln Menlo Park, CA, 1972. 

Physical Data bp 63-65.5 °C/2 mmHg 1.104 gcm . Solubility soluble in most organic solvents and partially soluble (approx. 11%) in water.  

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Synthesis of Acetyl Ethyl Disulfides. S- Ethyl ethanethiosulfinate can be rapidly converted to acetyl ethyl disulfide In moderate yield by reaction with thioacetic acid (eq 10). Advantageously, the liberated ethylsulfenic acid can regenerate the thiosulfinate via dehydration. Acetyl ethyl disulfide is a key intermediate for the synthesis of the ethyl hydrodisulfides, which can be prepared by acid catalyzed hydrolysis. 

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