Synthesis and structure of stilbene crowns.

✍ Scribed by Julian Tirado-Rives; Richard David Gandour; Frank Rolf Fronczek

• Book ID: 104220677
• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 238 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87178-6

✦ Synopsis

Syntheses of r-and ~-[a,el-dibenzo-7,10,13-trioxacyclotrideca-l,3,5-triene, 1 (n=l and E-and Z-[a,e]-dibenzo-7,10,13,16-tetraoxacyclohexadeca-l,3,Etriene, ,J rn=2) are described and the X-ray structure of E-J (n=l) is reported. As part of a program to develop new chemical models for enzymatic catalysis, stilbene molecules in which the aromatic rings are restricted from rotating are desired. This restriction should be readily accomplished by linking the 2,2' positions with an appropriate bridging moiety. Recent advances in synthetic methods for polyether podands2 and for cyclo-alkenes3 have suggested a straightforward approach to the desired molecules. This letter reports the facile two-step syntheses of a mixture of double bond isomers of stilbene crown ethers 4 (n=1,2) viz., E-and Z-[a,e]-dibenzo-7,10,13-trioxacyclotrideca-1,3,5-triene