ISSN:
1434-193X
Keywords:
Photoresponsive molecular switches
;
Norbornadiene
;
Quadricyclane
;
Polyethers
;
Complex ligands
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A Diels-Alder, retro Diels-Alder sequence provides access to 2,3,5-tri- and 2,3,5,6-tetraester-substituted norbornadienes. Attempts to reduce the norbornadiene esters with LiAlH4 failed. The corresponding quadricyclanes, which are available by photoisomerization of the norbornadienes give the alcohols in 32 and 74% yield. The quadricyclane alcohols 2a-c are converted with methyl iodide to compounds 3a-c or with 2-methoxyethyl 4-toluenesulfonate to the “tentacle molecules” 4a-c. A number of catalysts were tested to reisomerize the “tentacle” quadricyclanes to the norbornadienes. Neutral aluminum oxide proved to be most effective. In preliminary studies the tentacle quadricyclanes exhibit excellent complexing properties for Na+ and K+, whereas the norbornadiene isomers are less effective complexing agents.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
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