118451-62-0Relevant academic research and scientific papers
An Attempted Synthesis of 1,2-Cyclopentadiene and Wurtz-Like Condensation Products in the Reaction of 1,2-Dibromocycloalkenes
Ceylan, Mustafa,Secen, Hasan,Sutbeyaz, Yaser
, p. 501 - 508 (2007/10/03)
Fluoride ion-promoted elimination of 2-bromo-3-trimethylsilyl cyclohexene 16 and 2-bromo-3-trimethylsilyl cycloheptene 17 has been successfully used for synthesis of strained six- and seven- membered cyclic allenes.When 2-bromo-3-trimethylsilyl cyclopentene 5 was submitted to fluoride ion-promoted elimination only Wurtz-like dimeric products 6 and 7 were obtained instead of the expected 1,2-cyclopentadiene 8.Interestingly, reaction of 2,3-dibromocyclopentene 4, 2,3-dibromocyclohexene 12, and 2,3-dibromocycloheptene 13 with zinc gave only Wurtz-like dimeric products, (6,7), (18,19) and (20,21), respectively.
