Novel Behavior of Thiiranium Radical Cation Intermediates. Reactions of Dimethyl Disulfide with Alkenes in the Presence of Pd(OAc)2

Novel Behavior of Thiiranium Radical Cation Intermediates. Reactions of Dimethyl Disulfide with Alkenes in the Presence of Pd(OAc)2

Reaction of dimethyl disulfide (1) with cyclohexene (2a) in AcOH in the presence of Pd(OAc)2 yields trans-1-acetoxy-2-methylcyclohexane (3a). The equivalent reactions with hex-1-ene (2b) and 2-methylpent-1-ene (2c) or 1-methylcyclohex-1-ene (2d) preferentially give anti-Markovnikov and Markovnikov a...

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Bibliographic Details
Main Authors: Shingo Iizuka, Junnichi Takatori, Hiroshi Takeuchi
Format: Article
Language:English
Published: MDPI AG 2000-07-01
Series:Molecules
Subjects:
Dimethyl disulfide
Palladium (II) acetate
Acetoxymethylthiolation
Thiiranium radical cation
Regioselectivity for SN2 ring-opening
Solvent effects
Thietanium radical cation
Skeletal rearrangement
Online Access:http://www.mdpi.com/1420-3049/5/7/916/

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http://www.mdpi.com/1420-3049/5/7/916/

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