Issue 17, 1998

Reactions involving hexafluoropropylene oxide: novel ring opening reactions and resolution of a racemic mixture of a bromofluoro ester, ultrasound mediated Reformatsky reactions and stereoselectivity

Abstract

A novel ring opening reaction of hexafluoropropylene oxide (HFPO) 1 with lithium bromide/zinc bromide and subsequent reaction of the resulting acyl fluoride with primary and secondary alcohols gave bromofluoro esters 2, 3, 4 and 7. Reaction of the corresponding acyl fluoride with water leads to acid 9 which on treatment with dehydroabietylamine 10 gave the diastereomeric salt 11. Resolution of 11 and subsequent hydrolysis and esterification reactions led to enantiomerically pure ester 12. Reformatsky reactions with 2 were studied which gave the alcohols 6 and 5. A Reformatsky reaction of 12 with formaldehyde afforded an alcohol 13 which is indicated by NMR spectroscopy in the presence of a chemical shift reagent to have proceeded stereoselectively.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1998, 2803-2812

Reactions involving hexafluoropropylene oxide: novel ring opening reactions and resolution of a racemic mixture of a bromofluoro ester, ultrasound mediated Reformatsky reactions and stereoselectivity

P. L. Coe, M. Löhr and C. Rochin, J. Chem. Soc., Perkin Trans. 1, 1998, 2803 DOI: 10.1039/A804097D

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