Synthesis of Photoresponsive Polyethers

✍ Scribed by Felix Starck; Peter G. Jones; Rainer Herges

• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 310 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199811)1998:11<2533::aid-ejoc2533>3.0.co;2-q

✦ Synopsis

A Diels-Alder, retro Diels-Alder sequence provides access to molecules" 4a-c. A number of catalysts were tested to reisomerize the "tentacle" quadricyclanes to the nor-2,3,5-tri-and 2,3,5,6-tetraester-substituted norbornadienes. Attempts to reduce the norbornadiene esters with LiAlH 4 bornadienes. Neutral aluminum oxide proved to be most effective. In preliminary studies the tentacle quadricyclanes failed. The corresponding quadricyclanes, which are available by photoisomerization of the norbornadienes give exhibit excellent complexing properties for Na + and K + , whereas the norbornadiene isomers are less effective the alcohols in 32 and 74% yield. The quadricyclane alcohols 2a-c are converted with methyl iodide to compounds 3a-c complexing agents. or with 2-methoxyethyl 4-toluenesulfonate to the "tentacle