Cationic transannular oligomerization of 1,5-cyclooctadiene

Abstract

Cationic transannular oligomerization of 1,5-cyclooctadiene (I) using BF3.OEt2 or AlCl3 catalysts was studied. The conversion rate reached a constant when AlCl3-I molar ratio >4.0 ?10-2., while the conversion rate increased with increasing BF3.OEt2-I molar ratio. The conversion rate of I decreased in the presence of water and the catalytic activity of AlCl3 was higher than that of BF3OEt2. The average mol. wt. of the oligomer was ~103 and the softening temperature was 140-160? Pyrolysis gas chromatog.-mass spectrometric anal. showed that the major pyrolytic products of I was bicyclo[3.3.0]octane. A mechanism for oligomerization of I was proposed.

Key words: MOLECULAR WEIGHT DISTRIBUTION, REACTION MECHANISM, ALUMINIUM CHLORIDE, STRUCTURAL ANALYSIS, SOLVENT EFFECT, NUMBER AVERAGE MOLECULAR WEIGHT, PERICYCLIZATION, OLIGOMERIZATION, CYCLOOCTADIENE P, CHROMATOGRAPHY-MASS SPECTROGRAPHY

CLC Number:

O631.3

Cite this article

YUAN CUIMING;YAN DEYUE;XU XIANGMING;WANG FUSONG. Cationic transannular oligomerization of 1,5-cyclooctadiene[J]. Acta Chimica Sinica, 1988, 46(9): 919-923.

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