TY - JOUR
T1 - Syntheses, structure analyses, and reactions of 1,3,5-trioxepanes and related compounds
AU - McCullough, Kevin J.
AU - Masuyama, Araki
AU - Morgan, Keith M.
AU - Nojima, Masatomo
AU - Okada, Yuji
AU - Satake, Syuzo
AU - Takeda, Shin Y.
PY - 1998/8/7
Y1 - 1998/8/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=33748724932&partnerID=8YFLogxK
M3 - Article
SN - 0300-922X
VL - 15
SP - 2353
EP - 2362
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 15
ER -