873-12-1Relevant articles and documents
Polyspiranes, 16. - Cascade Rearrangements, 11. - Synthesis, Structure, Conformation, and Dynamics of Heptacyclo1,5.05,9.09,13.013,17.017,21>tetracosane (Coronane)
Wehle, Detlef,Schormann, Norbert,Fitjer, Lutz
, p. 2171 - 2178 (2007/10/02)
Coronane (2) was synthesized by addition of allylmagnesium bromide to ketone 7, rearrangement of the resulting homoallyl alcohol 8a to diene 9, hydrozirconization of 9 followed by bromination to give 11, and finally radical cyclization of 11.A direct cyclization of 9 using tri(n-butyl)tin hydride failed. 2 is all-cis-configurated, adopts a chair conformation in the crystal state and in solution and exhibits an extremely low barrier of inversion (ΔG(excit.)173 /= 8.6 kcal/mol).