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The reaction of 1,2-cyclononadiene with peracetic acid

โœ Scribed by W.Preston Reeves; Gary G. Stroebel

Publisher
Elsevier Science
Year
1971
Tongue
French
Weight
157 KB
Volume
12
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

In recent years several papers have appeared describing the peracid oxidation of allenes. 3,4,5,6 However, none of these reports have been concerned with cyclic allenes.

!Je wish to report the reaction of 1,2-cyclononadiene with peracetic acid. Treatment of 1,2-cyclononadiene with three (3) equivalents of acid-free 403 peracetic' in methylene chloride for 40 hours resulted in a quantitative conversion into 1,2-cyclononanedione and cyclooctene oxide in a ratio of 60:40. 0 CH3COOOH + 0 Roth products were isolated by preparative gas chromatography using a 20 ft. column of Carbowax fiOO0 on Chromasorb W. The structure of cvclooctene oxide was established by comparing infrared, mass spectra, and nmra with an authentic sample prepared by peracid epoxidation of cyclooctene.

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