TY - JOUR
T1 - Stereoelectronically‐programmed molecular ‘lego’ sets
AU - Ellwood, Paul
AU - Mathlas, John P.
AU - Fraser Stoddart, J.
AU - Kohnke, Franz H.
PY - 1988
Y1 - 1988
N2 - 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.
AB - 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.
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U2 - 10.1002/bscb.19880970807
DO - 10.1002/bscb.19880970807
M3 - Article
AN - SCOPUS:84988119861
SN - 0037-9646
VL - 97
SP - 669
EP - 678
JO - Bulletin des Sociétés Chimiques Belges
JF - Bulletin des Sociétés Chimiques Belges
IS - 8-9
ER -