Peroxidation of S-(2-Methyl-2-propyl) 2-Methyl-2-propanesulfinothioate

DOI: 10.1021/jo00241a025

Source and publish data:

Journal of Organic Chemistry p. 1263 - 1266 (1988)

Update date:2022-08-04

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Authors:

Freeman, Fillmore

Lee, Choonsun

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Article abstract of DOI:10.1021/jo00241a025

Oxidation of 1 equiv of S-(2-methyl-2-propyl) 2-methyl-2-propanesulfinothioate (1) with 2 equiv of m-chloroperoxybenzoic acid (MCPBA) gives S-(2-methyl-2-propyl) 2-methyl-2-propanesulfonothioate (4, 13percent), 2-methyl-2-propanesulfenic 2-methyl-2-propanesolfonic thioanhydride (5, 32percent), 2-methyl-2-propyl-3-chlorobenzoate (11, 4percent), 2-methyl-2-propyl 2-methyl-2-propanesulfinate (12, 22percent), and small amounts of bis(2-methyl-2-propyl) trisulfide (7) and bis(2-methyl-2-propyl) tetrasulfide (10).Possible mechanisms for product formation are discussed.

Full text of DOI:10.1021/jo00241a025

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