CUED Publications database

Stereochemistry of the C-S bond cleavage in cis-2-methylcyclopentyl phenyl sulfoxide radical cation.

Baciocchi, E and Lanzalunga, O and Lapi, A and Maggini, L (2009) Stereochemistry of the C-S bond cleavage in cis-2-methylcyclopentyl phenyl sulfoxide radical cation. J Org Chem, 74. pp. 1805-1808.

Full text not available from this repository.

Abstract

The TiO(2) photocatalyzed oxidation of cis-2-methylcyclopentyl phenyl sulfoxide in the presence of Ag(2)SO(4) in MeCN/H(2)O leads to the formation of 1-methylcyclopentanol, 1-methylcyclopentyl acetamide, and phenyl benzenethiosulfonate as the main reaction products. It is suggested that the C-S heterolysis in the radical cation is an unimolecular process leading to an ion radical pair. Fast 1,2-hydride shift in the secondary carbocation leads to 1-methylcyclopentyl carbocation that forms the observed products by reaction with H(2)O and MeCN. Attack of H(2)O on the ion radical pair may also occur, but as a minor route (<3%), with formation of trans-2-methylcyclopentanol.

Item Type: Article
Uncontrolled Keywords: Carbon Catalysis Cyclopentanes Oxidation-Reduction Photolysis Stereoisomerism Sulfoxides Sulfur Titanium
Subjects: UNSPECIFIED
Divisions: Div E > Manufacturing Systems
Depositing User: Cron Job
Date Deposited: 17 Jul 2017 19:24
Last Modified: 17 Aug 2017 01:25
DOI: