REARRANGEMENT ACCOMPANYING ADDITION OF FLUORINE TO 1,1-DIARYLETHYLENES
REARRANGEMENT ACCOMPANYING ADDITION OF FLUORINE TO 1,1-DIARYLETHYLENES
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DOI：
10.1021/ja00894a016
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发表时间：
1963-01-01
影响因子：
15
通讯作者：
NUNES, F
中科院分区：
文献类型：
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作者：
BORNSTEIN, J;BORDEN, R;NUNES, F
早期研究人员对1，1-二苯基乙烯和1，1-二苯基-1-丙烯加成生成的二氟化物的结构已被证明是不正确的；实际上，异构化重排产物a，-二氟联苯(VI)和1，L-二氟-1，2-二苯基丙烷(XIII)是分别形成的。1，1-二苯基乙烯与四氟化铅进行加成二聚反应生成1，4-二氟-1，1，4，4-四苯基丁烷(XIX)。讨论了一种可能的反应机理，该反应符合这种迄今未检测到的二聚体的独特结构，并涉及自由基中间体中的苯迁移。
The structures assigned by earlier investigators to the difluorides produced by the addition of fluorine to 1, 1-diphenylethylene and 1, 1-diphenyl-1-propene have been shown to be incorrect; actually, the isomericrearrange-ment products, a,-difluorobibenzyl (VI) and 1, l-difluoro-1, 2-diphenylpropane (XIII), respectively, are formed. It has been found that 1, 1-diphenylethylene also undergoes additive dimerization on fluorination with lead tetra-fluoride to yield 1, 4-difluoro-1, 1, 4, 4-tetraphenylbutane (XIX). A possible reaction mechanism consistent with the unique structure of this heretofore undetected dimer and involving phenyl migration in a free radicalintermediate is discussed.