Rigid face-to-face [3.3]-oo′-cyclophanes arene/alkene and arene/arene photocycloaddition reactions

✍ Scribed by Regina Thiergardt; Manfred Keller; Markus Wollenweber; Horst Prinzbach

• Book ID: 104215810
• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 327 KB
• Volume: 34
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79165-9

✦ Synopsis

Institut fiir Organische Chemie und Biochemie AlbeRstr. 21, D-7800 keiburg Summary. Proximity as origia of unusual ph0tOxeactivity is baii cxplorcd: In the naphtbdenc 5 (X-my analysis), direct or scnsitkcd photaxcitaticn induct an &icicnt mkx&ition to the naphthalmc nuti, otik+3is not cnibrced. Naphthoknm cyc@ti to, however, is pkto&micauy "inut". Structurally mlatcd bau&x.s 4 and 17 undcrgc phokx@ibraticn (2: 1) with the respective [6+2]+yclc&iucts. Cycloadditions to aromatic rings, particularly arenekene photodimerizations, make up a syntheGcaUy as well as theoreticslly attractive chapter of organic photochemistry.2 To us, the discovery of the ~photoequilibration Aa e Ba3 became of utmost importance as key step in our pagodane + do-route (C + D).4 Subsequent studies uncovered a very delicate structure dependancy for this o.o'-photocycloaddition: It similarly occurred in Ab,d (+ Bb,d) but not in Ac.5