289906-34-9Relevant academic research and scientific papers
Structural Factors for the Formation of Propellane-Type Products in the Solvolysis of Bicyclic Bridgehead Compounds
Tokunaga, Kazuhiko,Tachibana, Seiichiro,Okazaki, Takao,Ohga, Yasushi,Kitagawa, Toshikazu,Takeuchi, Ken'ichi
, p. 4964 - 4972 (2000)
Methanolyses of 2-oxobicyclo[3.3.1]non-1-yl triflate, 3,3-dimethyl-2-oxobicyclo[3.3.1]non-1-yl triflate, and 2-oxobicyclo[4.3.1]dec-1-yl mesylate gave the corresponding propellanone in 12%, 20%, or 3.2% yield, respectively, beside substitution or rearranged products under typical conditions. No propellane-type product was obtained in the solvolyses of 1-bromobicyclo[3.3.1]nonane, 2-methylidenebicyclo[3.3.1]non-1-yl heptafluorobutyrate, and 3,3-dimethyl-2-thioxobicyclo[3.3.1]non-1-yl tosylate. The factors that permit the formation of the propellane-type product from the intermediate bridgehead cations are examined with the aid of theoretical calculations at PM3 and B3LYP/6-31G*.
