112043-92-2Relevant academic research and scientific papers
13C-13C Coupling Constants in Bridgehead Polycycloalkanecarboxylic Acids
Della, Ernest W.,Gangodawila, Hemakanthi,Pigou, Paul E.
, p. 592 - 596 (1988)
A series of bicyclic and polycyclic systems substituted with the 13C-labeled carboxyl group at the bridgehead have been synthesized for 13C NMR analysis.It is found that one-bond coupling to the bridgehead carbon atoms shows a reasonable correlation with s character.Vicinal coupling to the unsubstituted bridgehead carbon in the bicyclic compounds was observed to be considerably smaller than anticipated.Calculated values of 3J(13C-13Cbridgehead) obtained by SCF MO calculations performed at the INDO level are in excellent agreement with those determined experimentally and demonstrate that the magnitude of 3J(C-C) is a reflection of opposing through-bond and through-space contributions.On the basis of the MO calculations, the large four-bond 13C-1H coupling in bicyclopentane-1-carboxylic-6-13C acid can be attributed almost entirely to the effect of through-space interactions.
Synthesis of Some Bridgehead-Bridgehead-Disubstituted Bicyclopentanes
Della, Ernest W.,Taylor, Dennis K.
, p. 2986 - 2996 (2007/10/02)
The synthesis of a wide variety of 1,3-disubstituted bicyclopentanes is described, with particular emphasis on the generation of a series of 3-X-substituted bicyclopentyl bromides required for solvolytic studies.Functional group manipulation at the bridgehead was readily accomplished in the majority of cases by radical processes; in some instances, transformations were effected via carbanionic-type intermediates.
