Syntheses, structure analyses, and reactions of 1,3,5-trioxepanes and related compounds

Kevin J. McCullough, Araki Masuyama, Keith M. Morgan, Masatomo Nojima, Yuji Okada, Syuzo Satake, Shin Y. Takeda

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10 Citations (Scopus)

Abstract

Acid-catalysed condensations of 1,5- or 1,6-dicarbonyl compounds with ethylene glycol give 1,3,5-trioxepane derivatives as a result of neighbouring participation by the adjacent carbonyl group during the acetalization process. With trimethylene glycol, the related 1,3,5-trioxocanes have also been obtained. Reaction of the 1,3,5-trioxepanes with (a) Grignard reagents gives dialkyl-substituted cyclic ethers, (b) titanium tetrachloride-allyltributyltin gives diallyl-substituted cyclic ethers and (c) triethylsilane in the presence of trimethylsilyl triflate provides the corresponding cyclic ethers.

Original languageEnglish
Pages (from-to)2353-2362
Number of pages10
JournalJournal of the Chemical Society, Perkin Transactions 1
Volume15
Issue number15
Publication statusPublished - 7 Aug 1998

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    McCullough, K. J., Masuyama, A., Morgan, K. M., Nojima, M., Okada, Y., Satake, S., & Takeda, S. Y. (1998). Syntheses, structure analyses, and reactions of 1,3,5-trioxepanes and related compounds. Journal of the Chemical Society, Perkin Transactions 1, 15(15), 2353-2362.