期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 128, 期 14, 页码 4703-4709出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja0566477
关键词
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Various cross-conjugated enediynes undergo Bergman-type cycloaromatizations upon reduction with potassium metal, generating anions of fulvenes and fulvalene derivatives. This new anionic cyclization is considerably more facile than the classic Bergman cyclization with linear enediynes, creating highly reactive diradicals at -78 degrees C. Not all cross-conjugated enediynes yield cyclized dianions upon reduction; some give uncyclized, Y-shaped, cross-conjugated dianions, while others apparently yield radical-anions that either dimerize or persist as monomers. One system yields both a cyclized and an uncyclized dianion. The substituents are thus shown to be a critical factor in determining the outcome of the reduction. Cyclization occurs within a specific window of opportunity that is governed by the substituents.
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