A new free-radical initiator, azobisisobutanol diacetate, has been prepared from azobisisobutyronitrile in good yield in three steps: ( 1 ) methanolysis to convert the nitrile groups to ester functions; (2) reduction of the diester to a diol; and (3) acetylation, Thus, it is more easily synthesized than other azo compounds having similar free-radical-generating properties and may be easily tagged with Cl4 if desired. Steady production of free radicals at 167" was demonstrated.
Dicyclohexylphosphine and diphenylphosphine react with 1,2-dichlorohexafluorocyclopentene to give almost exclusively the monoderivative via displacement of a vinylic chlorine atom. With the former phosphine a disubstituted derivative is also found. In addition to analytical values and infrared spectroscopic data, both I9F and 31P nuclear magnetic resonance spectra support the proposed structures.
A B S T R A C T T h e reaction o f methoxide ion with perfluorocyclopentene gave two major components. These have been identified as 1-fluoro-2-methoxyhexaAuorocyclopentene ( I I f ) and 1,2-dimethoxyhexafluorocyclopentene (IIe).A third component (3-methoxy-2,4,4,5,5-pentaAuoro-2-cyclopenten-l-one ( V I I ) ) was isoIated and a structure is proposed based on n.m.r. evidence.A list o f carbon-carbon double bond stretch frequencies is given for a number of 1,2-disubstituted perfluorocycloper~ter~es which follow the electronegativities o f the atoms adjacent t o the double bond.
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