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Issue 9, 2012
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Synthesis of renewable plasticizer alcohols by formal anti-Markovnikov hydration of terminal branched chain alkenesvia a borane-free oxidation/reduction sequence

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Abstract

An efficient method for the formal anti-Markovnikov hydration of 1,1-disubstituted alkenes has been developed. The utility of the process has been demonstrated by conversion of bio-derived butene oligomers into primary alcohols through initial oxidation to vicinal acetoxy-alcohols, diols, or diacetates, followed by selective dehydration/tautomerization of the diols, and hydrogenation of the intermediary aldehydes. This approach allows for the isolation of important industrial plasticizer alcohols from a renewable source. In a broader context, this pathway, which can be conducted with sustainable, conventional reagents under mild conditions, represents a unique alternative to hydroboration for a challenging subset of hindered olefins.

Graphical abstract: Synthesis of renewable plasticizer alcohols by formal anti-Markovnikov hydration of terminal branched chain alkenes via a borane-free oxidation/reduction sequence

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Article information


Submitted
18 Apr 2012
Accepted
19 Jun 2012
First published
20 Jun 2012

Green Chem., 2012,14, 2450-2456
Article type
Paper

Synthesis of renewable plasticizer alcohols by formal anti-Markovnikov hydration of terminal branched chain alkenes via a borane-free oxidation/reduction sequence

B. G. Harvey, H. A. Meylemans and R. L. Quintana, Green Chem., 2012, 14, 2450
DOI: 10.1039/C2GC35595G

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