Abstract
Electron transfer reactions of α-organothio-substituted heteroatom compounds lead to the cleavage of the C-S bond and the introduction of nucleophiles to the carbon. For example, It has been reported that the oxidation of α-organothio ethers in acetic acid results in the cleavage of the carbon-sulfur bond and the introduction of the acetoxyl group onto the carbon.1 The anodic oxidation of aorganothio ethers in methanol also gives the dimethyl acetal.2 In the anodic oxidation of benzyl sulfides, the C-S bond is cleaved and a nucleophile is introduced onto the carbon.3 Photoelectron transfer is also effective to cleave the carbon-sulfur bond.4
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
T. Mandai, H. Irie, M. Kawada, J. Otera, Tetrahedron Lett, 25, 2371 (1984).
J. Yoshida, S. Isoe, Chem. Lett., 631 (1987).
M. Kimura, Y. Yamamoto, Y. Sawaki, Denki Kagaku, 61, 862 (1993).
I. Saito, M. Takayama, T. Sakurai, J. Am. Chem. Soc., 116, 2653 (1994).
a) J. Yoshida, M. Sugawara, N. Kise, Tetrahedron Lett, 37, 3157 (1996).
M. Sugawara, K. Mori, J. Yoshida, Electrochimica Acta, 42, 1995 (1997).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1998 Springer Japan
About this paper
Cite this paper
Yoshida, Ji., Sugawara, M., Imagawa, M. (1998). The Mechanism of the C-S Bond Cleavage in Electron Transfer Reactions of α-Organothio-Substituted Heteroatom Compounds. In: Torii, S. (eds) Novel Trends in Electroorganic Synthesis. Springer, Tokyo. https://doi.org/10.1007/978-4-431-65924-2_19
Download citation
DOI: https://doi.org/10.1007/978-4-431-65924-2_19
Publisher Name: Springer, Tokyo
Print ISBN: 978-4-431-65926-6
Online ISBN: 978-4-431-65924-2
eBook Packages: Springer Book Archive