Efficient Alkylation Methods for the Synthesis of Hybrid Fluorocarbon–Hydrocarbon Tetrazoles as Potential Fluorinated Surfactants

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Contents Vol 63(5)

doi:10.1071/CH10005

Efficient Alkylation Methods for the Synthesis of Hybrid Fluorocarbon–Hydrocarbon Tetrazoles as Potential Fluorinated Surfactants

Yangen Huang ^A, Roger W. Read ^A ^B, Xiaobei Wang ^A

^A School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.
^B Corresponding author. Email: r.read@unsw.edu.au





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Australian Journal of Chemistry 63(5) 802–807 http://dx.doi.org/10.1071/CH10005
Submitted: 4 January 2010 Accepted: 16 February 2010 Published online: 21 May 2010

Abstract

The first 1,5- and 2,5-disubstituted fluorous tetrazoles are sought as potential surfactants. Direct alkylation of monosubstituted tetrazoles using alkyl iodides and triflates is compared with the Mitsunobu reaction. Mitsunobu conditions provide advantage for perfluoroalkylethylation, in terms of selectivity towards the 2,5-isomers and overall yield, but are not applicable to perfluoroalkylmethylation.