38262-52-1Relevant articles and documents
Hydrogenation of [5]- and [6]metacyclophane: Reactivity and thermochemistry
Van Eis, Maurice J.,Wijsman, Geerlig W.,De Wolf, Willem H.,Bickelhaupt, Friedrich,Rogers, Donald W.,Kooijman, Huub,Spek, Anthony L.
, p. 1537 - 1546 (2007/10/03)
The course of the hydrogenation of [5]- and [6]metacyclophane (1b and 1c) and their thermochemistry is described. Both compounds are hydrogenated rapidly (within 10 s) to furnish the bridgehead olefins 13b and 12c. The accompanying hydrogenation enthalpies are -220 and -141 kJ mol-1, respectively. Strain energies (SE) and olefinic strains (OS) of a number of bridgehead olefins have been evaluated by DFT calculations; it was concluded that 13b belongs to the class of hyperstable olefins which correlates nicely with its reluctance to undergo hydrogenation. By combining experimental hydrogenation enthalpies and DFT calculations, SE of 187 and 121 kJ mol-1 were derived for 1b and 1c.
