13755-04-9Relevant academic research and scientific papers
The Preparation and Some Reactions of Tricyclotetradecane-2,7-dione (Propellane-2,7-dione): X-Ray Crystal Structure of 2,7-bis(trimethylsilyloxy)tetracyclo2,7>tetradecane
Alder, Roger W.,Arrowsmith, Richard J.,Bryce, Martin R.,Eastment, Paul,Orpen, A. Guy
, p. 1519 - 1524 (2007/10/02)
Tricyclotetradecane-2,7-dione (1) has been made by reductive alkylation of bicyclodec-1-ene-2,7-dione, using Na-NH3 and Br(CH2)4Br.Reduction of (1) with sodium-potassium alloy in benzene in the presence of chlorotrimethylsilane yields 2,7-bis(trimethylsilyloxy)tetracyclo2,7>tetradecane (13), whose crystal structure is reported.Reduction of (1) with LiAlH4 and with Na-NH3-ButOH-THF gave mixtures of the three possible diastereoisomeric diols (15)-(17), which could not be separated, but whose isomeric composition could be estimated by (13)Cn.m.r. spectroscopy.Conformational equilibria in dione (1) and in diol (15) are discussed with the aid of force field calculations.
An Efficient General Method for Synthesis of Propellane and 11-Methyl-propellane
Pramod, Kakumanu,Rao, G. S. R. Subba
, p. 984 - 988 (2007/10/02)
A general method for the synthesis of propellane and 11-methyl-propellane is described.Thus the exo-alcohol (6) obtained by the addition of vinylmagnesiumbromide to the tricyclic enone (5) smoothly undergoes an Oxy-Cope rearrangement to the propellane derivative (8) which is transformed into the propellane.Similarly 11-methyl-propellane has been obtained from exo-alcohol (17).
