132202-40-5Relevant academic research and scientific papers
Experiments towards the Generation of 1,5- and 2,3-Didehydroquadricyclanes
Heywang, Ulrich,Szeimies, Guenter
, p. 121 - 131 (2007/10/02)
Metalation of the (hydroxymethyl)quadricyclanes 7a - c with n-butyllithium in ether is determined mostly by the chelating effect of the CH2O-Li group and only to a lesser extent by the magnitude of the 13C-1H coupling constant of the position to be lithiated in the corresponding quadricyclane derivative.Similar results were obtained for 3-quadricyclanol (20a).Treatment of the bromide 26a, prepared by lithiation of 7b, with strong bases apparently generates the 1,2-didehydroquadricyclane 34.and not the 1,5-didehydroquadricyclane 35.Attempts to convert the dihalide 9 into the 2,3-didehydroquadricyclane 4 were unsuccessful.
