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Efficient Two-Step Synthesis of 11,11'-Dithiobis[1-(2-bromo-2-methylpropionyloxy)undecane], a Conventional Initiator for Grafting Polymer Brushes from Gold Surfaces via ATRP

Belegrinou, Serena and Malinova, Violeta and Masciadri, Raffaello and Meier, Wolfgang. (2010) Efficient Two-Step Synthesis of 11,11'-Dithiobis[1-(2-bromo-2-methylpropionyloxy)undecane], a Conventional Initiator for Grafting Polymer Brushes from Gold Surfaces via ATRP. Synthetic communications, Vol. 40, H. 20. pp. 3000-3007.

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Official URL: http://edoc.unibas.ch/dok/A5841679

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Abstract

11,11'-Dithiobis[1-(2-bromo-2-methylpropionyloxy)undecane], a conventional initiator for grafting polymers from gold surfaces, was synthesized in two steps from 11-mercapto-1-undecanol in 88-92% overall yield. Oxidative dimerization of 11-mercapto-1-undecanol with a catalytic amt. of sodium iodide and 30% hydrogen peroxide in Et acetate proceeded in 96% yield. Esterification with 2-bromoisobutyryl bromide in dichloromethane was clean and almost quant. (92% yield) with pyridine used as base, whereas triethylamine gave a messy reaction (64% yield). Alternatively, esterification with 2-bromo-2-methyl-propanoic acid in dichloromethane occurred readily under Steglich's conditions with N,N'-dicyclohexylcarbodiimide (DCC) and a catalytic amt. of dimethylaminopyridine (DMAP; 88% yield). [on SciFinder(R)]
Faculties and Departments:05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Chemie > Makromolekulare Chemie (Meier)
UniBasel Contributors:Meier, Wolfgang P.
Item Type:Article, refereed
Article Subtype:Research Article
Bibsysno:Link to catalogue
ISSN:0039-7911
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:14 Sep 2012 07:19
Deposited On:14 Sep 2012 06:58

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