Strategy for the Synthesis of Tube‐Shaped Molecules

Abstract

3: 'H NMR (200 MHz, CDCI,, TMS): 6 = 8.9 (m, 8 H ; ppyrrole), 8.5 (d, 1 H; 8.2 (m, 6H; 8.0 (d, 1 H ; 7.8 (m, 10H; p,phenyl; p'-phenyl), 7.5 (t, 1 H; m-phenyl), -2.8 (NH pyrrole), 1.9-0.0 (6 m, 28H; CH,, 3 H,O, NHC=O, cyclam and lateral arm); I3C NMR (50.33 MHz, CDCI,, TMS): 6

Selective Synthesis of [12]Cycloparaphenylene

“…[1,2] Particularly interesting and challenging among these are aromatic belts [1] and rings as exemplified by the Vögtle belts, [3,4] cyclophenacenes, [5,6] cycloparaphenylenes, [7][8][9] and cyclacenes [10,11] . [1,2] Particularly interesting and challenging among these are aromatic belts [1] and rings as exemplified by the Vögtle belts, [3,4] cyclophenacenes, [5,6] cycloparaphenylenes, [7][8][9] and cyclacenes [10,11] .…”

“…We anticipated that the treatment of 7 with acid would lead to a sequence of 1) removal of the [b] [Pd(PtBu 3 ) 2 ] NaOH (5), H 2 O (5) 1 5 (18 %), 6 (27 %) 2 [c] [Pd(PtBu 3 ) 2 ] NaOH (5), H 2 O (5) 1 oligomerization 3 [c] [Pd(PtBu 3 ) 2 ] NaOH (5), H 2 O (5) 10 6 (28 %) 4 [c] [Pd(PtBu 3 ) 2 ] NaOH (5), H 2 O (16) 10 6 (43 %) 5 [c] [Pd(PPh 3 ) 4 ] NaOH (5), H 2 O (16) 10 6 (40 %) 6 [c] [PdCl 2 (dppf)] NaOH (5), H 2 O (16) 10 6 (67 %) 7 [d] [PdCl 2 (dppf)] NaOH (5) [d] 1 [b] PPh 3 MOM groups, 2) eight-fold dehydration (dihydroxycyclohexane!cyclohexadiene), and 3) oxidation (cyclohexadiene! We anticipated that the treatment of 7 with acid would lead to a sequence of 1) removal of the [b] [Pd(PtBu 3 ) 2 ] NaOH (5), H 2 O (5) 1 5 (18 %), 6 (27 %) 2 [c] [Pd(PtBu 3 ) 2 ] NaOH (5), H 2 O (5) 1 oligomerization 3 [c] [Pd(PtBu 3 ) 2 ] NaOH (5), H 2 O (5) 10 6 (28 %) 4 [c] [Pd(PtBu 3 ) 2 ] NaOH (5), H 2 O (16) 10 6 (43 %) 5 [c] [Pd(PPh 3 ) 4 ] NaOH (5), H 2 O (16) 10 6 (40 %) 6 [c] [PdCl 2 (dppf)] NaOH (5), H 2 O (16) 10 6 (67 %) 7 [d] [PdCl 2 (dppf)] NaOH (5) [d] 1 [b] PPh 3 MOM groups, 2) eight-fold dehydration (dihydroxycyclohexane!cyclohexadiene), and 3) oxidation (cyclohexadiene!…”

The Supramolecular Chemistry of Strained Carbon Nanohoops

“…Although the first attempts to prepare [ n ]cycloparaphenylenes ( [ n ]CPPs ) go back to 1934 and the [ n ]cyclacenes were first proposed in 1954, it took until the 1980s before Vögtle and others systematically attempted to prepare nanohoops such as the CPPs and all‐annelated macrocycles such as the “Vögtle belts” . Although none of the synthetic attempts ultimately led to success, these early reports provided much conceptual inspiration and even included the preparation of the 1,4‐disubstituted cyclohexanes that were later used by Itami and co‐workers as intermediates in the preparation of CPPs …”

Nanometre‐Scale Molecular Ribbons

“…For example, 10a according to conventional phane nomenclature is named 5,7,95,97-tetrakis- (4,6)(1,3)benzeno < 9 > phane. As the components in the middle part of the molecules are listed repeatedly, we propose to put the repeating sequences in braces and use a multiplier to indicate the number of repititions.…”