Stereoelectronically‐programmed molecular ‘lego’ sets

Paul Ellwood*, John P. Mathlas, J. Fraser Stoddart, Franz H. Kohnke

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

The observation that the syn‐isomer 1 of 1,4:5,8‐diepoxy‐1,4,5,8‐tetrahydroanthracene becomes involved in a series of highly diastereoselective Diels‐Alder reactions with 2,3,5,6‐tetramethylene‐7‐oxabicyclo[2.2.1]heptane 2 to form, in excellent overall yield, the novel macropolycyclic compound 6 ‐ a potential precursor of [12]beltene 7, [12]collarene 8, [12]cyclacene 9, and the perhydro[12]cyclacene derivative 10 ‐ is interpreted in terms of the stereoelectronic characteristics of the dienophilic components of 1 and the diene components of 2, and obvious steric factors, combining to favour one particular stereochemistry out of eight possibilities for the transition states involving each of the four different cycloaddition steps.

Original languageEnglish (US)
Pages (from-to)669-678
Number of pages10
JournalBulletin des Sociétés Chimiques Belges
Volume97
Issue number8-9
DOIs
StatePublished - 1988

ASJC Scopus subject areas

  • Chemistry(all)

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