Preparation of 9,9-Dihydro-9-Hydroxyperfluoro 3,6-Dioxa-5-Methyl-l-Nonene

Preparation of 9,9-Dihydro-9-Hydroxyperfluoro-(3,6-Dioxa-5-Methyl-l-Nonene) (5) 

Tetramethylammonium chloride (2 mg) and 5 (1. Og) were placed in a vial, sealed, and heated in an oil bath at 107°C for 65 h. H-NMR analysis of the colorless, viscous grease showed the ratio of signals at 4.6 and 3.90ppm as ca. 60/1. The small amount of cyclic dimer formed (GC anlaysis) was removed by Kugelrohr distillation (up to 100°C/0.05 mm). 19F-NMR featured the internal/ terminal CF2CH20 group ratio as ca. 83/1. Size-exclusion chromatography showed the major peak with Mn, =26,700 and Mw =52,800, consistent with condensation polymer 7. 

CAUTION. Fluorine is a strong oxidizer and a very corrosive material. An appropriate vacuum line made from copper or Monel in a well-ventilated area should be constructed for working with this element. The reactions themselves were carried out in Teflon vessels. If elementary precautions are taken, work with fluorine is relatively simple. 

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