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Molecular Belts and Collars in the Making: A Hexaepoxyoctacosahydro[12]cyclacene Derivative
Author(s) -
Kohnke Franz H.,
Slawin Alexandra M. Z.,
Stoddart J. Fraser,
Williams David J.
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198708921
Subject(s) - yield (engineering) , derivative (finance) , stereoselectivity , product (mathematics) , high pressure , cover (algebra) , chemistry , computational chemistry , mathematics , materials science , organic chemistry , physics , engineering , engineering physics , geometry , composite material , mechanical engineering , catalysis , financial economics , economics
Repeated Diels–Alder reactions of the suitably curved and stiff reactants 1 and 2 furnish, via the central intermediate 3 , the intellectually appealing title (and cover page) compound. In the last step of the synthesis, 3 is allowed to react with 2 under high pressure (9–10 kbar). The yield is nevertheless 20%. The Diels–Alder reactions are remarkably stereoselective, the intermediates are topologically extremely interesting, and the final product—it speaks for itself.