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

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 diaceta...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2012-08, Vol.14 (9), p.2450-2456
Main Authors: Harvey, Benjamin G, Meylemans, Heather A, Quintana, Roxanne L
Format: Article
Language:English
Subjects:
Alcohols
Aldehydes
Alkenes
Butenes
Diols
Hydration
Oxidation
Plasticizers
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Summary: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.
ISSN:1463-9262
1463-9270
DOI:10.1039/c2gc35595g