有機合成化学協会誌
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
CF3基で安定化された芳香族化合物の原子価結合異性体の化学
小林 義郎熊懐 稜丸榛沢 雄二
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ジャーナル フリー

1979 年 37 巻 3 号 p. 183-196

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Trifluoromethyl group shows a stabilizing effect on the compounds which would be unstable if they had no trifluoromethyl group. This review is concerned with two faces of the chemistry of trifluoromethylated valence bond isomers of aromatic compounds : Diels-Alder and 1, 3-dipolar reactions planned for the conversion of hexakis (trifluoromethyl) benzvalene to the corresponding tetrahedrane and the synthesis of new valence bond isomers of heteroaromatic compounds. In the former, the tetrahedrane itself could not yet be isolated, but the formation of tetrakis (trifluoromethyl) cyclobutadiene and new valence isomers of oxepin was confirmed. In the latter, Dewar thiopene, Dewar pyrrole, Dewar pyridine, and diphosphabenzvalene with trifluoromethyl groups were synthesized and their reactions were discussed. The effect of trifluoromethyl group is not limited to the strained compound. Thus, tetrakis (trifluoromethyl) -1, 4-diphosphabenzene, the first example of diphosphabenzenes, was synthesized.

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