Clear-cut difference in the rearrangement of 1-bromo-2-(2-phenyl-3-butenyl)benzene under anionic or radical conditions
作者:Céline Reynaud、Hassan Hazimeh、Jean-Marc Mattalia、Caroline Marchi-Delapierre、Michel Chanon
DOI:10.3998/ark.5550190.0012.a03
日期:——
o-(3-butenyl)phenyl system bearing a phenyl group on the 2-position of the side chain was studied as a potential mechanistic probe for distinguishing between radical and carbanion intermediates. The Bu3SnH reduction of 1-bromo-2-(2-phenyl-3-butenyl)benzene, 4, yields mainly the 1,5-cyclization product, 6, with a preference for the transisomer. Treatment of 4 with Mg or t-BuLi leads to double-bond isomerization
研究了在侧链的 2-位上带有苯基的邻(3-丁烯基)苯基体系作为区分自由基和碳负离子中间体的潜在机制探针。1-溴-2-(2-苯基-3-丁烯基)苯 4 的 Bu3SnH 还原主要产生 1,5-环化产物 6,优先生成转异构体。用 Mg 或 t-BuLi 处理 4 导致双键异构化并产生 (E)-1,2-二苯基-2-丁烯 8,以及 3,4-二苯基-1-丁烯 5。