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Beilstein J. Org. Chem. 2011, 7, 278–289, doi:10.3762/bjoc.7.37
Graphical Abstract
Scheme 1: Photorearrangements of dibenzobarrelenes 1a and 1b.
Scheme 2: Stereoselective DPM rearrangement of chiral salts in the solid-state.
Scheme 3: Synthesis of ureido- and thioureido-substituted dibenzobarrelene derivatives 1e–i.
Scheme 4: Di-π-methane rearrangements of ureido- and thioureido-substituted dibenzobarrelene derivatives 1h a...
Figure 1: Photometric titration of A) tetrabutylammonium chloride (TBAC) to 1h (c1h = 50 µM) and of B) tetrab...
Figure 2: Structures of chiral additives employed in DPM rearrangements.
Figure 3: Structure of anthracene–thiourea conjugate 4.
Figure 4: Proposed structure of the complex between 1h and mandelate SMD.
Beilstein J. Org. Chem. 2011, 7, 119–126, doi:10.3762/bjoc.7.17
Scheme 1: Photorearrangements of dibenzobarrelene (DBB).
Figure 1: General structure of pyrrolidinium-annelated dibenzosemibullvalenes (pyDBS).
Scheme 2: Synthesis of dibenzobarrelene derivatives 2a–g.
Scheme 3: Di-π-methane rearrangements of dibenzobarrelene derivatives 2a–f (counter ions omitted for clarity)....
Scheme 4: Di-π-methane rearrangement of dibenzobarrelene derivative 2g.
Scheme 5: Synthesis and solid-state photoreactivity of the sulfonate salt 2b-4.
Scheme 6: Phase-transfer catalyzed alkylation reactions (see Table 1 for details).